Holdings: Science of synthesis

Science of synthesis: Houben-Weyl methods of molecular transformations 28 = Category 4, Compounds with two carbon-heteroatom bonds Quinones and heteroatom analogues

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Bibliographic Details
Main Author:	Avendaño, C. (Author)
Other Authors:	Griesbeck, Axel G. (Editor)
Format:	Book
Language:	English
Published:	Stuttgart [u.a.] Thieme 2006
Subjects:	Chemische Synthese Chinone
Online Access:	Inhaltsverzeichnis
Physical Description:	XL, 1006 Seiten Illustrationen 26 cm
ISBN:	3131187913 1588904601 9783131187918

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245	1	0	\|a Science of synthesis \|b Houben-Weyl methods of molecular transformations \|n 28 = Category 4, Compounds with two carbon-heteroatom bonds \|p Quinones and heteroatom analogues \|c ed. board: D. Bellus ...
264		1	\|a Stuttgart [u.a.] \|b Thieme \|c 2006
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adam_text	^^^^.^ _™™_ XIII Table of Contents Introduction A. G. Griesbeck Introduction 1 28.1 Product Class 1: Benzo 1,4 quinones 28.1.1 Product Subclass 1: Metal Substituted Benzo 1,4 quinones B. G. Vong and E. A. Theodorakis 28.1.1 Product Subclass 1: Metal Substituted Benzo 1,4 quinones 13 28.1.1.1 Synthesis of Product Subclass 1 14 28.1.1.1.1 Method 1: Tin Substituted Benzo 1,4 quinones by Cyclobutenone Ring Expansion 14 28.1.1.1.2 Method 2: Tin Substituted Benzo 1,4 quinones by Stannylation of Benzo 1,4 quinones 16 28.1.1.1.3 Method 3: Silicon Substituted Benzo 1,4 quinones by Reaction of Organolithium Species 16 28.1.1.1.4 Method 4: Silicon Substituted Benzo 1,4 quinones by Cyclobutenone Ring Expansion 17 28.1.1.1.5 Method 5: Silicon Substituted Benzo 1,4 quinones by Carbene Annulation 20 28.1.1.1.6 Method 6: Silicon Substituted Benzo 1,4 quinones by Nucleophilic Substitution 21 28.1.1.1.7 Method 7: Boron Substituted Benzo 1,4 quinones by Carbene Benzannulation 22 28.1.1.2 Applications of Product Subclass 1 in Organic Synthesis 22 28.1.1.2.1 Method 1: Palladium Catalyzed Cross Coupling Reactions of Tin Substituted Benzo 1,4 quinones 22 28.1.1.2.1.1 Variation 1: Allylation 23 28.1.1.2.1.2 Variation 2: Coupling with Aromatic and Heteroaromatic Iodides 23 28.1.1.2.1.3 Variation 3: Oxidative Dimerization 25 28.1.1.2.1.4 Variation 4: Benzannulation 26 28.1.1.2.2 Method 2: Silicon/Halide Exchange Reactions of Silicon Substituted Benzo 1,4 quinones 27 28.1.1.2.3 Method 3: Oxidation of the Boron Substituent in Boron Substituted Benzo 1,4 quinones 28 XIV Table of Contents 28.1.2 Product Subclass 2: Halogen Substituted Benzo 1,4 quinones M. Balci, M. Celik, and M. S. Gultekin 28.1.2 Product Subclass 2: Halogen Substituted Benzo 1,4 quinones 31 28.1.2.1 Monohalobenzo 1,4 quinones 31 28.1.2.1.1 Synthesis of Monohalobenzo 1,4 quinones 31 28.1.2.1.1.1 Method 1: Oxidation of 4 Amino 3 iodophenol Using Potassium Dichromate 31 28.1.2.1.1.2 Method 2: Oxidation of 1,4 Hydroquinones with Persulfate or Ammonium Cerium(IV) Nitrate 32 28.1.2.1.1.3 Method 3: Oxidation of 1,4 Hydroquinones Catalyzed by an Oxovanadium Complex 34 28.1.2.1.1.4 Method 4: Oxidation of 1,4 Hydroquinones Catalyzed by Caseous Nitrogen Oxides 34 28.1.2.1.1.5 Methods 5: Miscellaneous Oxidations of Anilines and 1,4 Hydroquinones 35 28.1.2.1.2 Applications of Monohalobenzo 1,4 quinones in Organic Synthesis 35 28.1.2.2 2,3 Dihalobenzo 1,4 quinones 39 28.1.2.2.1 Synthesis of 2,3 Dihalobenzo 1,4 quinones 39 28.1.2.2.1.1 Methodi: Halogenation of Benzo 1,4 quinone 39 28.1.2.2.1.2 Method 2: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate 41 28.1.2.2.2 Applications of 2,3 Dihalobenzo 1,4 quinones in Organic Synthesis 41 28.1.2.3 2,5 Dihalobenzo 1,4 quinones 42 28.1.2.3.1 Synthesis of 2,5 Dihalobenzo 1,4 quinones 42 28.1.2.3.1.1 Methodi: Oxidation of 1,2,4,5 Tetrafluorobenzene 42 28.1.2.3.1.2 Method 2: Oxidation of 1,4 Hydroquinones 43 28.1.2.3.1.3 Method 3: Oxidative Demethylation of 1,4 Dimethoxybenzenes 43 28.1.2.4 2,6 Dihalobenzo 1,4 quinones 43 28.1.2.4.1 Synthesis of 2,6 Dihalobenzo 1,4 quinones 43 28.1.2.4.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones Catalyzed by Metalated Phthalocyanines 43 28.1.2.4.1.2 Method 2: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate 44 28.1.2.4.1.3 Method 3: Oxidation of Phenols Using Metal Oxides 44 28.1.2.4.2 Applications of 2,6 Dihalobenzo 1,4 quinones in Organic Synthesis 45 28.1.2.5 2,3,5 Trihalobenzo 1,4 quinones 46 28.1.2.5.1 Synthesis of 2,3,5 Trihalobenzo 1,4 quinones 46 28.1.2.5.1.1 Methodi: Halogenation of Benzo 1,4 quinones 46 28.1.2.5.1.2 Method 2: Bromination of 2,5 Dichlorobenzo 1,4 quinone 46 28.1.2.5.1.3 Method 3: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate 47 28.1.2.5.2 Applications of 2,3,5 Trihalobenzo 1,4 quinones in Organic Synthesis 47 Table of Contents XV 28.1.2.6 2,3.5,6 Tetrahalobenzo 1,4 quinones 48 28.1.2.6.1 Synthesis of 2,3,5,6 Tetrahalobenzo 1,4 quinones 48 28.1.2.6.1.1 Method 1: Halogenation of Benzo 1,4 quinone 48 28.1.2.6.1.2 Method 2: Oxidation of 1,4 Hydroquinones Using Hydrogen Peroxide or Chlorine 49 28.1.2.6.1.3 Method 3: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate, and Other Reactions 49 28.1.2.6.2 Applications of 2,3,5,6 Tetrahalobenzo 1,4 quinones in Organic Synthesis — 49 28.1.3 Product Subclass 3: Chalcogen Substituted Benzo 1,4 quinones S. H. Kim and E. A. Theodorakis 28.1.3 Product Subclass 3: Chalcogen Substituted Benzo 1,4 quinones 53 28.1.3.1 Synthesis of Product Subclass 3 54 28.1.3.1.1 Method 1: Oxidative Dearomatization 54 28.1.3.1.1.1 Variation 1: Oxidation of Chalcogen Substituted Phenols 54 28.1.3.1.1.2 Variation 2: Oxidation of Chalcogen Substituted Hydroquinones 56 28.1.3.1.1.3 Variation 3: Oxidative Demethylation of Chalcogen Substituted Hydroquinone Mono and Diethers 57 28.1.3.1.1.4 Variation 4: Miscellaneous Oxidations 58 28.1.3.1.2 Method 2: Nucleophilic Additions on the Benzoquinone Motif 59 28.1.3.1.2.1 Variation 1: Conjugate Addition/Oxidation 59 28.1.3.1.2.2 Variation 2: Conjugate Addition Elimination 61 28.1.3.1.3 Method 3: Ring Expansion of Cyclobutenediones 61 28.1.3.2 Applications of Product Subclass 3 in Organic Synthesis 64 28.1.3.2.1 Method 1: Cycloaddition Reactions of Chalcogen Substituted Benzo 1,4 quinones 64 28.1.3.2.2 Method 2: Conjugate Additions of Chalcogen Substituted Benzo 1,4 quinones 66 28.1.4 Product Subclass 4: Nitrogen and Phosphorus Substituted Benzo 1,4 quinones H. Lee and E. A. Theodorakis 28.1.4 Product Subclass 4: Nitrogen and Phosphorus Substituted Benzo 1,4 quinones 71 28.1.4.1 Synthesis of Product Subclass 4 71 28.1.4.1.1 Method 1: Nitrogen Substituted Benzo 1,4 quinones by Nucleophilic Addition/Oxidation 71 28.1.4.1.2 Method 2: Nitrogen Substituted Benzo 1,4 quinones by Nucleophilic Substitution 74 28.1.4.1.3 Method 3: Nitrogen Substituted Benzo 1,4 quinones by Oxidation of a Benzene Ring 75 XVI Table of Contents 28.1.4.1.4 Method 4: Phosphorus Substituted Benzo 1,4 quinones by Addition/Elimination and Addition/Oxidation Sequences — 76 28.1.4.2 Applications of Product Subclass 4 in Organic Synthesis 77 28.1.4.2.1 Method 1: Ring Contraction of Benzoquinones 77 28.1.4.2.1.1 Variation 1: Synthesis of Cyclopentenediones from Azidoquinones 77 28.1.4.2.1.2 Variation 2: Synthesis of Butenolides from Azidoquinones 78 28.1.4.2.1.3 Variation 3: Cyanoketenes from Aminoquinones and Their Use in Synthesis 79 28.1.4.2.2 Method 2: Formation of Oxazoles 80 28.1.4.2.3 Method 3: Synthesis of Hetarene Fused Benzo 1,4 quinones 82 28.1.5 Product Subclass 5: Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Heteroatoms M. Balci, M. Celik, and M. S. Cultekin 28.1.5 Product Subclass 5: Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Heteroatoms 87 28.1.5.1 Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Halogens 87 28.1.5.1.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Halogens 88 28.1.5.1.1.1 Method 1: Oxidation of Phenols with Chlorous Acid 88 28.1.5.1.1.2 Method 2: Oxidation of Phenols with Manganese(IV) Oxide 88 28.1.5.1.1.3 Method 3: Oxidative Demethylation of Dimethoxybenzenes 89 28.1.5.1.1.4 Method 4: Oxidative Debenzylation of Bis(benzyloxy)benzenes 90 28.1.5.2 Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Oxygen 91 28.1.5.2.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Oxygen 92 28.1.5.2.1.1 Method 1: Oxidation of Hydroquinones with Ammonium Cerium(IV) Salts 92 28.1.5.2.1.2 Method 2: Oxidation of Hydroquinones with Silver(ll) Oxide 93 28.1.5.2.1.3 Method 3: Oxidation of Hydroquinones with Polymer Supported (Diacetoxyiodo)benzene 94 28.1.5.2.1.4 Method 4: Oxidative Demethylation of Dimethoxybenzenes 94 28.1.5.2.1.5 Method 5: Reaction of Maleoylcobalt Complexes with Alkynes 95 28.1.5.3 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen and One Bond to Nitrogen 96 28.1.5.3.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen and One Bond to Nitrogen 98 28.1.5.3.1.1 Method 1: Oxidation of Hydroquinones with Ammonium Cerium(IV) Nitrate 98 28.1.5.3.1.2 Method 2: Oxidation of Hydroquinones with Silver(l) Oxide 98 28.1.5.3.1.3 Method 3: Oxidation of Hydroquinones with Fungal Laccase 98 28.1.5.3.1.4 Method 4: Oxidative Demethylation of Dimethoxybenzenes 99 28.1.5.4 Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Nitrogen 101 Table of Contents XVII 28.1.5.4.1 Synthesis of Benzol ,4 quinones Substituted with Carbon with Three Bonds to Nitrogen 101 28.1.5.4.1.1 Method 1: Oxidation of Hydroquinones with Silver Salts 101 28.1.5.4.1.2 Method 2: Oxidation of Hydroquinones with Manganese(IV) Oxide 102 28.1.6 Product Subclass 6: Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Heteroatoms M. Balci, M. Celik, and M. S. Giiltekin 28.1.6 Product Subclass 6: Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Heteroatoms 105 28.1.6.1 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Halogens 105 28.1.6.1.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Halogens 105 28.1.6.1.1.1 Method 1: Oxidative Demethylation of a 1,4 Dimethoxybenzene 105 28.1.6.2 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen — 106 28.1.6.2.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen 106 28.1.6.2.1.1 Method 1: Oxidation of 1,4 Hydroquinones with Silver(l) Oxide 106 28.1.6.2.1.2 Method 2: Oxidation of 1,4 Hydroquinones with Manganese(IV) Oxide 108 28.1.6.2.1.3 Method 3: Oxidation of a 1,4 Hydroquinone with 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone 109 28.1.6.2.1.4 Method 4: Oxidation of a 1,4 Hydroquinone Derivative in Aqueous Media 110 28.1.6.2.1.5 Method 5: Oxidative Demethylation of 1,4 Dimethoxybenzenes 110 28.1.6.2.2 Applications of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen in Organic Synthesis 111 28.1.6.3 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Nitrogen •¦• 112 28.1.6.3.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Nitrogen 112 28.1.6.3.1.1 Method 1: Oxidation of a Diol with Manganese(IV) Oxide 112 28.1.7 Product Subclass 7: Benzo 1,4 quinones Substituted with Carbon with One Bond to a Heteroatom M. Balci, M. S. Gultekin, and M. Celik 28.1.7 Product Subclass 7: Benzo 1,4 quinones Substituted with Carbon with One Bond to a Heteroatom 115 28.1.7.1 Benzo 1,4 quinones Substituted with Carbon with One Bond to a Halogen •¦¦ 115 28.1.7.1.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with One Bond to a Halogen 115 28.1.7.1.1.1 Method 1: Demethylation of 1,4 Dimethoxybenzenes by Electrochemical Oxidation 115 XVIII Table of Contents 28.1.7.1.1.2 Method 2: Demethylation of Dimethoxybenzenes by Oxidation with Ammonium Cerium(IV) Nitrate 116 28.1.7.1.1.3 Method 3: Demethylation of Dimethoxybenzenes by Oxidation with Nitric Acid 116 28.1.7.1.1.4 Method 4: Allylic Bromination and Substitution 117 28.1.7.2 Benzo 1,4 quinones Substituted with Carbon with One Bond to Oxygen 119 28.1.7.2.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with One Bond to Oxygen 119 28.1.7.2.1.1 Method 1: (Diacetoxyiodo)benzene Oxidation 119 28.1.7.2.1.2 Method 2: Oxidation of Anilines 120 28.1.7.2.1.3 Method 3: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Nitric Acid 120 28.1.7.2.1.4 Method 4: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Ammonium Cerium(IV) Nitrate 121 28.1.7.2.1.5 Method 5: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Silver(l) Oxide 122 28.1.7.2.1.6 Method 6: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Iron(lll) Chloride 125 28.1.7.2.1.7 Methods 7: Additional Methods 126 28.1.7.3 Benzo 1,4 quinones Substituted with Carbon with One Bond to Sulfur 129 28.1.7.3.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with One Bond to Sulfur 129 28.1.8 Product Subclass 8: Alkynyl , Aryl , and Alkenyl Substituted Benzo 1,4 quinones M. Balci, M. S. Giiltekin, and M. Celik 28.1.8 Product Subclass 8: Alkynyl , Aryl , and Alkenyl Substituted Benzo 1,4 quinones 131 28.1.8.1 Alkynyl Substituted Benzo 1,4 quinones 131 28.1.8.1.1 Synthesis of Alkynyl Substituted Benzo 1,4 quinones 131 28.1.8.1.1.1 Method 1: Suzuki Cross Coupling of Benzo 1,4 quinones 131 28.1.8.1.1.2 Method 2: Oxidative Demethylation of 1,4 Dimethoxybenzenes 132 28.1.8.1.1.3 Method 3: Addition of Organolithium Compounds to Benzoquinone Derivatives 134 28.1.8.1.1.3.1 Variation 1: Addition to 2,5 Dialkoxybenzo 1,4 quinones 134 28.1.8.1.1.3.2 Variation 2: Addition to Dimethoxybenzo 1,2 quinones 135 28.1.8.2 Aryl Substituted Benzo 1,4 quinones 137 28.1.8.2.1 Synthesis of Aryl Substituted Benzo 1,4 quinones 137 28.1.8.2.1.1 Method 1: Coupling Reactions of Benzo 1,4 quinones 137 28.1.8.2.1.2 Method 2: Oxidative Demethylation and Coupling of a 1,4 Dimethoxybenzene 139 28.1.8.2.1.3 Method 3: Oxidation of 1,4 Hydroquinones Catalyzed by an Oxovanadium Complex 139 Table of Contents XIX 28.1.8.2.1.4 Method 4: Oxidation of Phenols and Derivatives Using Metals and Metal Oxides 140 28.1.8.2.1.5 Method 5: Oxidation of Phenols with Fremy's Salt 141 28.1.8.2.1.6 Method 6: Reaction of Fischer Carbene Complexes with Phenylacetylenes 142 28.1.8.2.1.7 Method 7: Reaction of Phenylacetylenes with a Tetracarbonyliron Species or with Carbon Monoxide 143 28.1.8.2.1.8 Methods 8: Additional Methods 144 28.1.8.3 Alkenyl Substituted Benzo 1,4 quinones 147 28.1.8.3.1 Synthesis of Alkenyl Substituted Benzo 1,4 quinones 147 28.1.8.3.1.1 Method 1: Direct Introduction of a Vinyl Group into Benzo 1,4 quinones 147 28.1.8.3.1.2 Method 2: Suzuki Cross Coupling of Benzo 1,4 quinones 147 28.1.8.3.1.3 Method 3: Oxidation of 1,4 Hydroquinones with Silver(l) Oxide 148 28.1.8.3.1.4 Method 4: Oxidation of a 1,4 Hydroquinone with 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone 149 28.1.8.3.1.5 Method 5: Oxidative Demethylation of 1,4 Dimethoxybenzenes with Ammonium Cerium(IV) Nitrate 150 28.1.8.3.1.6 Method 6: Electrochemical Oxidation of 1,4 Dimethoxybenzenes 150 28.1.8.3.1.7 Method 7: Thermal Ring Expansion of Cyclobutenedione Derivatives •¦• 151 28.1.8.3.1.8 Methods 8: Additional Methods 152 28.1.9 Product Subclass 9: Alkyl Substituted Benzo 1,4 quinones M. Balci, M. S. CGItekin, and M. Celik 28.1.9 Product Subclass 9: Alkyl Substituted Benzo 1,4 quinones 157 28.1.9.1 Monoalkylbenzo 1,4 quinones 157 28.1.9.1.1 Synthesis of Monoalkylbenzo 1,4 quinones 157 28.1.9.1.1.1 Method 1: Coupling Reactions of Benzo 1,4 quinones 157 28.1.9.1.1.2 Method 2: Oxidation of 1,4 Hydroquinones with an Organoselenium Reagent 158 28.1.9.1.1.3 Method 3: Oxidation of 1,4 Hydroquinones with Ammonium Cerium(IV) Nitrate 159 28.1.9.1.1.4 Method 4: Oxidation of Phenols and Derivatives 160 28.1.9.2 2,3 Dialkylbenzo 1,4 quinones 161 28.1.9.2.1 Synthesis of 2,3 Dialkylbenzo 1,4 quinones 161 28.1.9.2.1.1 Method 1: Oxidation of a 1,4 Hydroquinone with Silver(l) Oxide 161 28.1.9.2.1.2 Method 2: Oxidation of N Arylsulfonamides 161 28.1.9.2.1.3 Method 3: Reaction of Fischer Carbene Complexes with Alkynes 162 28.1.9.2.1.4 Methods 4: Additional Methods 162 28.1.9.3 2,5 Dialkylbenzo 1,4 quinones 165 28.1.9.3.1 Synthesis of 2,5 Dialkylbenzo 1,4 quinones 165 28.1.9.3.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones Using Methyltrioxorhenium(VII) 165 XX Table of Contents 28.1.9.3.1.2 Method 2: Oxidation of 1,4 Hydroquinones with Polymer Supported (Diacetoxyiodo)benzene 166 28.1.9.3.1.3 Method 3: Oxidation of 1,4 Hydroquinones and Derivatives with Ammonium Cerium(IV) Nitrate or Pyridinium Chlorochromate 166 28.1.9.3.1.4 Methods 4: Additional Methods 168 28.1.9.4 2,6 Dialkylbenzo 1,4 quinones 170 28.1.9.4.1 Synthesis of 2,6 Dialkylbenzo 1,4 quinones 170 28.1.9.4.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones 170 28.1.9.4.1.2 Method 2: Reaction of Acetylenes with a Carbonyliron Species 172 28.1.9.5 2,3,5 Trialkylbenzo 1,4 quinones 173 28.1.9.5.1 Synthesis of 2,3,5 Trialkylbenzo 1,4 quinones 173 28.1.9.5.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones 173 28.1.9.5.1.2 Methods 2: Additional Methods 174 28.1.9.6 2,3,5,6 Tetraalkylbenzo 1,4 quinones 175 28.1.9.6.1 Synthesis of 2,3,5,6 Tetraalkylbenzo 1,4 quinones 175 28.1.9.6.1.1 Method 1: Oxidation of 1,4 Hydroquinones and Derivatives 175 28.2 Product Class 2: Benzo 1,2 quinones V. Nair and K. V. Radhakrishnan 28.2 Product Class 2: Benzo 1,2 quinones 181 28.2.1 Synthesis of Product Class 2 182 28.2.11 Method 1: Oxidation of Catechols Using Silver(l) Salts 182 28.2.1.2 Method 2: Oxidation of Catechols Using Cerium(IV) Reagents 183 28.2.1.3 Method 3: Oxidation of Catechols Using Periodate Salts 184 28.2.14 Method 4: Oxidation of Catechols Using N Chlorosuccinimide 184 28.2.1.5 Method 5: Oxidation of Catechols Using Other Reagents 185 28.2.1.6 Method 6: Oxidation of Phenols Using Benzeneseleninic Anhydride 185 28J.U Method 7: Oxidation of Phenols Using Fremy's Salt 186 28.2.1.8 Method 8: Oxidation of Phenols Using Other Reagents 187 28.2.2 Applications of Product Class 2 in Organic Synthesis 187 28.2.2.1 Method 1: Addition of Nucleophiles 187 28.2.2.2 Method 2: Diels Alder and Related Reactions 195 28.2.2.2.1 Variation 1: Benzo 1,2 quinones as Carbodienes and Heterodienes 195 28.2.2.2.2 Variation 2: Benzo 1,2 quinones as Dienophiles 196 28.2.2.2.3 Variation 3: Benzo 1,2 quinones as Heterodienophiles 198 28.2.2 3 Method 3: Dipolar Cydoadditions 198 28J.2.3.1 Variation 1: Nitrile Oxide Addition 198 28.2.2.3.2 Variation 2: Diazomethane Addition 200 28J.2.3.3 Variation 3: Acyclic Carbonyl Ylide Addition 200 28.2.2.3.4 Variation 4: Cyclic Carbonyl Ylide Addition 201 28.2.2.3.5 Variation 5: Addition of Mesoionic Compounds 202 28.2.2.3.6 Variation 6: Addition of Phosphorus Ylides 204 Table of Contents XXI 28.2.2 4 Method 4: Multicomponent Reactions 205 28.2.2.4.1 Variation 1: Addition of Zwitterions Generated from Isocyanides and Dimethyl Acetylenedicarboxylate 205 28.2.2.4.2 Variation 2: Addition of Zwitterions Generated from Dialkoxycarbenes and Dimethyl Acetylenedicarboxylate 207 28.2.2.5 Methods 5: Additional Methods 208 283 Product Class 3: Naphtho 1,4 quinones E. A. Couladouros and A. T. Strongilos 283 Product Class 3: Naphtho 1,4 quinones 217 283.1 Synthesis of Product Class 3 220 283.1.1 Synthesis by Ring Closure Reactions 220 283.1.1.1 Method 1: Reaction of Fischer Type Carbene Complexes with Alkynes 220 283.1.1.2 Method 2: Synthesis from Cyclobutenediones 225 283.1.1.2.1 Variation 1: Reaction of Phthaloyl Complexes with Functionalized Alkynes 229 283.1.1.3 Method 3: Annulation Reactions of Phthalide Anions with Michael Acceptors 232 283.1.1.4 Method 4: [4+ 2] Cycloaddition Reactions 234 283.1.1.4.1 Variation 1: Reaction of Benzo 1,4 quinones with Heterosubstituted Dienes 239 283.1.1.4.2 Variation 2: Reaction of Benzo 1,4 quinones with Vinylarenes and Vinylhetarenes 241 283.1.1.4.3 Variation 3: Reaction of Benzo 1,4 quinones with Dienes of Fixed s cis Conformation 242 283.1.1.4.4 Variation 4: Quinones as Dienes 245 283.1.1.5 Method 5: Condensation of Benzaldehydes with Succinic Acid Derivatives 246 283.1.1.6 Method 6: Friedel Crafts Condensation of Hydroquinone Derivatives with Maleic Anhydrides 248 283.1.1.7 Method 7: Annulation of ortho Substituted Tertiary Benzamides 250 283.1.2 Synthesis by Oxidative Transformation 251 283.1.2.1 Method 1: Oxidation of Naphthalenes 252 283.1.2.1.1 Variation 1: Oxidation of Naphthalene Derivatives Bearing Oxidation Directing Groups 255 283.1.2.2 Method 2: Oxidation of Naphthols 255 283.1.2.3 Method 3: Oxidation of Hydroquinone Derivatives 261 283.1.2.3.1 Variation 1: Oxidation of Diprotected Hydroquinone Derivatives 261 283.1.2.3.2 Variation 2: Oxidation of Monoprotected Hydroquinone Derivatives 263 283.1.2.3.3 Variation 3: Oxidation of Hydroquinones 264 283.1.2.4 Method 4: Oxidation of Naphthols Bearing Substituents Other Than Oxygen at the 4 Position 265 283.1.2.5 Method 5: Aromatization and Benzylic Oxidation of Fused Carbocycles 267 283.1.3 Substitution of Hydrogen 267 283.1.3.1 Method 1: Using Nucleophilic Carbon Reagents 268 XXII Table of Contents 283.1.3.2 Method 2: Using Electrophilic Carbon Reagents 271 28.3.13 3 Method 3: Using Carbon Free Radicals 273 283.1.3.4 Method 4: Addition of Halides 277 283.1.3.5 Method 5: Varvoglis' lodonium Ylides 279 283.1.3.6 Method 6: Using Oxygen Nucleophiles 280 283.1.3.7 Method 7: TheThiele Winter Acetoxylation Reaction 282 283.1.3.8 Method 8: Using Sulfur Nucleophiles 283 283.1.3.9 Method 9: Addition of Amines, Azides, and Ammonia 286 283.1.4 Substitution of Heteroatoms 289 283.1.4.1 Method 1: Substitution of Halogen by Another Halogen 289 283.1.4.2 Method 2: Substitution of Halogen by Oxygen 289 283.1.4.3 Method 3: Substitution of Halogen by Sulfur 291 283.1.4.4 Method 4: Substitution of Halogen by Nitrogen 292 283.1.4.5 Method5: Substitution of Halogen by Carbon 294 283.1.4.5.1 Variation 1: Palladium Mediated Coupling of Halogenated Naphtho 1,4 quinones 295 283.1.4.6 Method 6: Substitution of Oxygen by Halogen, Nitrogen, or Carbon — 297 28.4 Product Class 4: Naphtho 1,2 , Naphtho 1,5 , Naphtho 1,7 , Naphtho 2,3 , and Naphtho 2,6 quinones C. C. Liao and R. K. Peddinti 28.4 Product Class 4: Naphtho 1,2 , Naphtho 1,5 , Naphtho 1,7 , Naphtho 2,3 , and Naphtho 2,6 quinones 323 28.4.1 Product Subclass 1: Naphtho 1,2 quinones 323 28.4.1.1 Synthesis of Product Subclass 1 325 28.4.1.1.1 Method 1: Reaction of Fischer Type Carbene Complexes with tert Butyl Isocyanide 325 28.4.1.1.2 Method 2: [4+ 2] Cycloaddition Reactions 325 28.4.1.1.2.1 Variation 1: Reaction of Benzoquinones with 2,3 Dimethylbuta 1,3 diene 325 28.4.1.1.2.2 Variation 2: Reaction of Dihalocatechols with 1 (Trimethylsiloxy)buta 1,3 diene 326 28.4.1.1.3 Method 3: Dieckmann Ring Formation with Subsequent Acyloin Cleavage 327 28.4.1.1.4 Method 4: Oxidation of a Tetralones 327 28.4.1.1.5 Method 5: Oxidation of Naphthalenes 328 28.4.1.1.6 Method 6: Oxidation of 1 Naphthols 329 28.4.1.1.6.1 Variation 1: Oxidation of 1 Naphthols with Fremy's Salt 329 28.4.1.1.6.2 Variation 2: Oxidation of 1 Naphthols with Benzeneseleninic Anhydride 332 28.4.1.1.6.3 Variation 3: Oxidation of 1 Naphthols with Cobalt Salen Complex/Oxygen 332 28.4.1.1.6.4 Variation 4: Synthesis of Emmotin H Using lodylbenzene 333 28.4.1.1.6.5 Variations: Oxidation of a 1 Naphthol Derivative with Sodium Periodate 333 28jI.i.i.6.6 Variation 6: Oxidation of Halo 1 naphthols with Lead(IV) Acetate 334 28^4.1.1.6.7 Variation 7: Transition Metal Catalyzed Oxidations of 1 Naphthols 334 28A1.1.7 Method 7: Oxidation of 2 Naphthols 336 Table of Contents XXIII 28.4.1.1.7.1 Variation 1: Oxidation of 2 Naphthol 336 28.4.1.1.7.2 Variation 2: Oxidation of 2 Naphthols with Fremy's Salt 336 28.4.1.1.7.3 Variation 3: Synthesis of o Hibiscanone with Benzeneseleninic Anhydride 337 28.4.1.1.7.4 Variation 4: Oxidation of 2 Naphthols with Copper Chloride/Oxygen 337 28.4.1.1.7.5 Variation 5: Oxidation of 2 Naphthols with 3 Chloroperoxybenzoic Acid 338 28.4.1.1.7.6 Variation 6: Transition Metal Catalyzed Oxidations of 2 Naphthols 339 28.4.1.1.7.7 Variation 7: Oxidation of 1 Amino 2 naphthol by Polymer Supported Hypochlorite Ion 339 28.4.1.1.8 Method 8: Oxidation of Naphthalene 1,2 diols 339 28.4.1.1.8.1 Variation 1: Oxidation of Naphthalene 1,2 diol 340 28.4.1.1.8.2 Variation 2: Synthesis from Naphthalene 1,2 diol Disilyl Ether 340 28.4.1.1.8.3 Variation 3: Aerial Oxidation of Naphthalene 1,2 diols 341 28.4.1.1.8.4 Variation 4: Synthesis of Saprorthoquinone via Silver(l) Oxide Oxidation 342 28.4.1.1.8.5 Variation 5: Oxidation of Naphthalene 1,2 diol with Oxygen and Bis(propane 1,3 diamine)copper(ll) Chloride 342 28.4.1.1.9 Method 9: Oxidation of a 1 Methoxynaphthalen 2 amine Derivative — 342 28.4.1.1.10 Method 10: Rearrangement of Naphtho 1,4 quinone Adducts 343 28.4.1.1.11 Method 11: Substitution of Hydrogen 343 28.4.1.1.11.1 Variation 1: Reaction of Naphtho 1,2 quinone with Pyrroles 343 28.4.1.1.11.2 Variation 2: Reaction of Naphtho 1,2 quinone with Vinylogous Michael Donors 344 28.4.1.1.11.3 Variation 3: Lewis Acid Mediated Reactions of Naphtho 1,2 quinones — 344 28.4.1.1.H.4 Variation 4: Palladium(ll) Catalyzed Oxidative Coupling of Naphtho 1,2 quinone and Arenes 345 28.4.1.1.11.5 Variation 5: Photochemical Reactions of Naphtho 1,2 quinones 345 28.4.1.1.11.6 Variation 6: Reactions of Naphtho 1,2 quinones with Amines 348 28.4.1.1.11.7 Variation 7: Reactions of 4 Aminonaphtho 1,2 quinone with Diazenes ¦•• 349 28.4.1.1.11.8 Variation 8: Metal Chloride Catalyzed Addition of Alcohols to Naphtho 1,2 quinones 350 28.4.1.1.11.9 Variation 9: Reactions of Naphtho 1,2 quinones with Thiols 351 28.4.1.1.12 Method 12: Substitution of Heteroatoms 351 28.4.1.1.12.1 Variation 1: Reactions of 4 Alkoxynaphtho 1,2 quinones with Amines ••• 351 28.4.1.1.12.2 Variation 2: Reactions of Sodium 4 Sulfonatonaphtho 1,2 quinone 352 28.4.1.1.13 Method 13: Alkylation of the Silver Salt of 2 Hydroxynaphtho 1,4 quinones 355 28.4.2 Product Subclass 2: Naphtho 1,5 quinones 356 28.4.2.1 Synthesis of Product Subclass 2 356 28.4.2.1.1 Method 1: Oxidation of a 2,3 Dihydronaphtho 1,4 quinone Imine 356 28.4.2.1.2 Method 2: Oxidation of Naphthalene 1,5 diols 356 28.4.2.1.2.1 Variation 1: Air Oxidation of a Naphthalene 1,5 diol 356 28.4.2.1.2.2 Variation 2: 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone Oxidation of 3,7 Di tert butylnaphthalene 1,5 diol357 28.4.2.1.3 Method 3: Substitution of Hydrogen by Halogen 357 28.4.2.1.3.1 Variation 1: Substitution of Hydrogen by Chlorine 357 28.4.2.1.3.2 Variation 2: Substitution of Hydrogen by Bromine 358 28.4.2.1.4 Method 4: Substitution of 4,8 Diaminonaphtho 1,5 quinone 358 XXIV Table of Contents 28.4.3 Product Subclass 3: Naphtho 1,7 quinones 358 28.4.3.1 Synthesis of Product Subclass 3 358 28.4.3.1.1 Method 1: 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone Oxidation of 3,6 Di tert butyl 8 methylnaphthalene 1,7 diol 358 28.4.4 Product Subclass 4: Naphtho 2,3 quinones 359 28.4.4.1 Synthesis of Product Subclass 4 359 28.4.4.1.1 Method 1: Generation and Trapping through Desilylation Debromination Induced by Fluoride Ion 359 28.4.4.1.2 Method 2: Oxidation of 1,4 Diarylnaphthalene 2,3 diols 360 28.4.5 Product Subclass 5: Naphtho 2,6 quinones 362 28.4.5.1 Synthesis of Product Subclass 5 362 28.4.5.1.1 Method 1: Photooxygenation of Naphthalen 2 amine 362 28.4.5.1.2 Method 2: Oxidation of a Naphthalene 2,6 diol with Lead(IV) Oxide • • • • 362 283 Product Class 5: Anthra 9,10 quinones, Anthra 1,2 quinones, Anthra 1,4 quinones, Anthra 2,9 quinones, and Their Higher Fused Analogues K. Krohn and N. Boker 28.5 Product Class 5: Anthra 9,10 quinones, Anthra 1,2 quinones, Anthra 1.4 quinones, Anthra 2,9 quinones, and Their Higher Fused Analogues 367 28.5.1 Product Subclass 1: Anthra 9,10 quinones 367 28.5.1.1 Synthesis of Product Subclass 1 369 28.5.1.1.1 Friedel Crafts Reactions 369 28.5.1.1.1.1 Method 1: One Pot Procedures Using Fused Salts (N Alkylpyridinium Halides) with Aluminum Trichloride as the Catalyst 371 28.5.1.1.1.2 Method 2: One Pot Procedures Using Molten Aluminum Trichloride Potassium Chloride Sodium Chloride or Aluminum Trichloride Sodium Chloride as the Catalysts 372 28.5.1.1.1.3 Method 3: One Pot Procedures Using Croup 4 or Croup 5 Metal Oxides as the Catalysts 373 28.5.1.1.1.4 Method 4: One Pot Procedures Using Phthaloyl Dichlorides as the Electrophiles 373 28.5.1.1.1.5 Method 5: Stepwise Procedures with Benzoylbenzoic Acids as the Intermediates 374 283.1.1.1.5.1 Variation 1: Benzoylbenzoic Acids by Friedel Crafts Reaction 375 28.5.1.1.1.5.2 Variation 2: Benzoylbenzoic Acids by Addition of Crignard Reagents to Phthalic Anhydrides 375 28.5.1.1.1.6 Method 6: Stepwise Procedures Involving Direct Cyclization of Benzoylbenzoic Acids 376 283.1.1.1.7 Method 7: Stepwise Procedures Involving Sequential Cyclization of Benzylbenzoic Acids and Oxidation 378 Table of Contents XXV 28.5.1.1.1.8 Method 8: Stepwise Procedures Involving Benzylbenzoic Acids Prepared by Displacement of a Methoxy Group in Aryldihydrooxazoles 380 28.5.1.1.1.9 Method 9: Stepwise Procedures Involving Friedel Crafts Type Alkylation of 3 Bromophthalides with Benzenes To Form 3 Arylphthalides 381 28.5.1.1.2 Diels Alder Reactions 382 28.5.1.1.2.1 Method 1: Reaction of Open Chain Dienes with Naphtho 1,4 quinones Followed by Elimination or Oxidation of Allylic Hydroxy Croups 383 28.5.1.1.2.2 Method 2: Reaction of Open Chain Dienes with Naphtho 1,4 quinones Followed by Two p Eliminations 388 28.5.1.1.2.2.1 Variation 1: Reaction of 1,3 Siloxy 1,3 dienes with Halonaphtho 1,4 quinones 388 28.5.1.1.2.2.2 Variation 2: Reaction of 1,3 Siloxy 1,3 dienes with Dichloronaphtho 1,4 quinones 390 28.5.1.1.2.2.3 Variation 3: Reaction of Vinylketene Acetals with 2 or3 Halonaphtho 1,4 quinones 391 28.5.1.1.2.2.4 Variation 4: Diels Alder Reactions of Sulfinylnaphtho 1,4 quinones 395 28.5.1.1.2.3 Method 3: Reaction of Cyclic Dienes with Naphtho 1,4 quinones, Followed by a Retro Diene Reaction 395 28.5.1.1.2.4 Method 4: Reaction of Cyclic Dienes with Naphtho 1,4 quinones Followed by Hydroxymethylation of 1,4 Ethanoanthra 9,10 quinones 399 28.5.1.1.2.5 Method 5: Reaction of Naphtho 1,4 quinones with Ketene Acetals 400 28.5.1.1.2.6 Method 6: Coupling of Naphtho 1,4 quinones with Cyclobutenones — 401 28.5.1.1.2.7 Method 7: Thermolytic Rearrangement of Arylcyclobutenones 401 28.5.1.1.2.8 Method 8: Electrocyclization of 2,3 Divinylnaphtho 1,4 quinones 402 28.5.1.1.2.9 Method 9: Electrocyclization of 2,3 Divinylnaphtho 1,4 quinones to 1,4 Diacylanthra 9,10 quinones 403 28.5.1.1.3 Ring Closing Metathesis 404 28.5.1.1.3.1 Method 1: Cyclization of 2,3 Diallylnaphtho 1,4 quinones 404 28.5.1.1.4 [2 + 2 + 2] Cycloaddition Reactions 406 28.5.1.1.4.1 Method 1: Rhodium Catalyzed Cycloaddition of 1,2 Dipropynoylbenzenes with Alkynes 406 28.5.1.1.5 Anionic Condensation Reactions 407 28.5.1.1.5.1 Method 1: Phthalide Annulation with Cyclohex 2 enones 407 28.5.1.1.5.2 Method 2: Phthalide Annulation with Cyclohexadienones 408 28.5.1.1.5.2.1 Variation 1: With Cyclohexa 2,5 dienones 409 28.5.1.1.5.2.2 Variation 2: With Cyclohexa 2,4 dienones 410 28.5.1.1.5.3 Method 3: Phthalide Annulation with Arynes 410 28.5.1.1.6 Cyclization by Nucleophilic Aromatic Substitution/Addition 411 28.5.1.1.6.1 Method 1: Cyclization of 2 (Cyanomethyl)benzophenones (The Hassall Reaction) 411 28J.1.1.6.2 Method 2: Addition of 2 (Cyanomethyl)benzoates to Arynes 412 28.5.1.1.6.3 Method 3: Cyclization of (Nitromethyl)benzophenones 413 XXVI Table of Contents 283.1.1.6.4 Method 4: Cyclization of Monoalkylnaphtho 1,4 quinones 414 28.5.1.1.6.5 Method 5: Cyclization of 2,3 Disubstituted Naphtho 1,4 quinones by Aldol Condensation 414 28.5.1.1.6.5.1 Variation 1: Michael Addition of 2 Acetylnaphtho 1,4 quinones 415 28.5.1.1.6.5.2 Variation 2: Base Induced Condensation of 2 Acylnaphtho 1,4 quinones 415 28.5.1.1.6.6 Method 6: Cyclization of 2,3 Dialkylnaphtho 1,4 quinones by Reaction of Enamines with 2 Acetylnaphtho 1,4 quinones ••• 416 28.5.1.1.6.7 Method 7: Cyclization of 2,3 Dialkylnaphtho 1,4 quinones by Iterative Addition of 1,3 Dicarbonyl Dianions 417 28.5.1.1.6.7.1 Variation 1: Addition of 1,3 Dicarbonyl Dianions to Homophthalic Diesters 417 28.5.1.1.6.7.2 Variation 2: Addition of 1,3 Dicarbonyl Dianions to Homophthalic Monoesters 418 28.5.1.1.7 Oxidation of Anthracenes to Anthra 9,10 quinones 419 28.5.1.1.7.1 Method 1: Catalytic Oxidation of Anthracene with Dioxygen in the Presence of Nitrogen Dioxide 420 28.5.1.1.7.2 Method 2: Transition Metal Catalyzed Liquid or Vapor Phase Aerial Oxidation of Anthracene 421 283.1.1.7.3 Method 3: Anodic Oxidation of Anthracene 421 283.1.1.7.4 Method 4: Catalytic Oxidation of Anthracene with Other Sources of Oxygen 422 283.1.1.7.5 Method 5: Stoichiometric Oxidations of Anthracene 423 283.1.1.8 Oxidative Cyclization Reactions of 2 Benzyl Substituted Diphenylmethanes 424 28.5.1.1.8.1 Methodi: Oxidation of 1 Benzyl 2 methylbenzene 424 283.1.1.9 Oxidation of Dihydroanthra 9,10 quinones or Anthracen 9(10H) ones to Anthra 9,10 quinones 424 283.1.1.9.1 Methodi: Aerial Oxidation of Anthracen 9(10H) one or 9,10 Dihydroanthracenes 424 283.1.1.9.2 Method 2: Oxidation of Anthracen 9(10H) ones, 10 Hydroxyanthracen 9(10H) ones, or Hydroquinone Methyl Ethers by Ammonium Cerium(IV) Nitrate 425 283.1.1.10 Oxidation of meso Benza nth rones and Aromatic Carbocycles 425 283.1.1.11 Alkylation Reactions 425 283.1.1.11.1 Methodi: Addition of Nitroalkanes to Hydroxyanthra 9,10 quinones ••• 426 283.1.1.11.2 Method 2: Addition of Malonate to Hydroxyanthra 9,10 quinones 426 283.1.1.11.3 Method 3: Alkylation of 1,4 Dihydroxyanthra 9,10 quinone via Anthracene 1,4,9,10 tetrone and a 1,5 Alkyl Shift 427 283.1.1.11.4 Method 4: Alkylation with Intermediate Reduction 427 283.1.1.11.4.1 Variation 1: Alkylation under Strongly Basic Conditions (Marschalk Conditions) 427 283.1.1.11.4.2 Variation 2: Alkylation with Piperidine Acetate as the Catalyst (Lewis Conditions) 429 283.1.1.11.4.3 Variation 3: Alkylation with Pyrrolidine as the Catalyst (Broadbent Conditions) 430 283.1.1.11.4.4 Variation 4: Hydroxyalkylation of peri Hydroxyanthra 9,10 quinones (Modified Marschalk Reaction) 431 Table of Contents XXVII 28.5.1.U1.4.5 Variation 5: 1,5 Oiazabicyclo[5.4.0]undec 7 ene or 1,5 Diazabicylo[4.3.0] non 5 ene in Tetrahydrofuran in Marschalk Reactions 432 28.5.1.1.11.4.6 Variation 6: Successive Marschalk Reactions in Syntheses of 2,3 Dialkylanthra 9,10 quinones 434 28.5.1.1.11.4.7 Variation 7: Addition of 1 Hydroxyanthra 9,10 quinones and Their Tautomers to Michael Acceptors 434 28.5.1.1.11.4.8 Variation 8: Alkylation of 1 Aminoanthra 9,10 quinones 435 28.5.1.1.11.4.9 Variation 9: Alkylation of 1 Hydroxyanthra 9,10 quinones 435 28.5.1.1.11.5 Method 5: Alkylation of Anthra 9,10 quinones by the Reductive Claisen Rearrangement 436 28.5.1.1.11.6 Method 6: Alkylation by a Combination of the Marschalk Reaction and the Reductive Claisen Rearrangement 437 28.5.1.1.11.7 Method 7: Alkylation via Diazonium Ions 438 28.5.1.1.12 Arylation Reactions 439 28.5.1.1.13 Alkenylation Reactions 439 28.5.1.1.14 Alkynylation Reactions 439 28.5.1.1.14.1 Methodi: Isomerization of Allylanthra 9,10 quinones 439 28.5.1.1.15 Halogenation Reactions 440 28.5.1.1.15.1 Methodi: Fluorination 440 28.5.1.1.15.2 Methodi: Chlorination 440 28.5.1.1.15.3 Method 3: Bromination 441 28.5.1.1.15.4 Method 4: lodination 443 28.5.1.1.16 Sulfonation Reactions 443 28.5.1.1.17 Amination Reactions 444 28.5.1.1.18 Hydroxylation Reactions 445 28.5.1.1.19 Nitration Reactions 445 28.5.1.1.20 Synthesis by Substitution 447 28.5.1.1.20.1 Methodi: Substitution of Fluoride 447 28.5.1.1.20.2 Method 2: Substitution of Chloride 448 28.5.1.1.20.3 Method 3: Substitution of Bromide or Iodide 450 28.5.1.1.20.3.1 Variation 1: Substitution of Bromide and Iodide by Heteroatoms 450 283.1.1.20.3.2 Variation 2: Substitution of Bromide by Aryl Croups (The Heck Reaction) 450 28.5.1.1.20.3.3 Variation 3: Substitution of Bromide and Iodide by Acetylene Nucleophiles 451 28.5.1.1.20.3.4 Variation 4: Substitution of Iodide with Tin Nucleophiles 453 28.5.1.1.20.4 Method 4: Substitution of Nitro Croups 453 28.5.1.1.20.5 Method 5: Substitution of Trifluoromethanesulfonates 454 28.5.2 Product Subclass 2: Anthra 1,2 quinones 455 28.5.2.1 Synthesis of Product Subclass 2 455 28.5.2.1.1 Oxidation Reactions 455 28.5.2.1.1.1 Methodi: Oxidation of 1,2 Dihydroxyanthracenes 455 28.5.2.1.1.2 Method 2: ortho Specific Oxygenation of 1 Anthrols 456 XXVIII Table of Contents 28.5.3 Product Subclass 3: Anthra 1,4 quinones 457 28.5.3.1 Synthesis of Product Subclass 3 457 28.5.3.1.1 Fixation of the 1,4 Dicarbonyl Tautomer of 1,4 Dihydroxyanthra 9,10 quinone 457 28.5.3.1.1.1 Method!: Chlorination of 1,4 Dihydroxyanthra 9,10 quinone 457 28.5.3.1.1.2 Method 2: Transesterification of N,O,O Triacylated 1,4 Dihydroxy 10 iminoanthracen 9(10H) ones 458 28.5.3.1.2 Diels Alder Reactions 458 28.5.3.1.2.1 Method 1: Addition of Quinodimethanes to Benzoquinones 458 28.5.3.1.2.2 Method 2: Strong Base Mediated Addition of Homophthalic Anhydrides to Benzoquinones 459 28.5.3.1.2.3 Method 3: Tandem Claisen Diels Alder Reactions 460 28.5.3.1.2.4 Method 4: Phthalide Annulation 461 28.5.4 Product Subclass 4: Anthra 2,9 quinones 461 28.5.5 Product Subclass 5: Anthraquinones Fused with Other Carbon Rings 462 283.5.1 Synthesis of Product Subclass 5 462 28.5.5.1.1 Synthesis of Anthraquinones Fused with Four Membered Rings 462 28.5.5.1.1.1 Method 1: Double Aldol Condensation 462 28.5.5.1.2 Synthesis of Anthraquinones Fused with Five Membered Rings 463 28.5.5.1.2.1 Method 1: Friedel Crafts Reaction of Phthalic Anhydride with Indanes 463 28.5.5.1.2.2 Method 2: Diels Alder Reactions of Naphtho 1,4 quinone with 1 Vinylcyclopentenes 463 28.5.5.1.2.3 Method 3: Cyclization of Monoalkylanthra 9,10 quinones 463 28.5.5.1.2.4 Method 4: Cyclization of 2,3 Dialkylanthra 9,10 quinones 464 28.5.5.1.3 Synthesis of Anthraquinones Fused with Six Membered Rings: Tetracene 5,12 diones 465 28.5.5.1.3.1 Method 1: One Pot Friedel Crafts Condensation 466 28.5.5.1.3.1.1 Variation 1: Double Friedel Crafts Condensation with Phthalic Anhydride 466 28.5.5.1.3.1.2 Variation 2: Successive Fries Shift and Friedel Crafts Reaction 466 28.5.5.1.3.2 Method 2: Multistep Friedel Crafts Condensation 467 28.5.5.1.3.2.1 Variation 1: Friedel Crafts Reaction of Benzylbenzoic Acids 467 28J.5.1.3.2.2 Variation 2: Friedel Crafts Reaction of a Lactone 468 28.5.5.1.3.2.3 Variation 3: Friedel Crafts Reaction of Benzoylbenzoic Acids 468 28.5.5.1.3.3 Method 3: Tetracene 5,12 diones by Diels Alder Reactions: Trapping of o Quinodimethanes with Dienes 469 28.5.5.1.3.3.1 Variation 1: Intermolecular Trapping of o Quinodimethanes 470 28.5.5.1.3.3.2 Variation 2: Intramolecular Trapping of o Quinodimethanes 471 28.5.5.1.3.4 Method 4: Diels Alder Reactions of Anthra 1,4 quinones and Derivatives as the Dienophiles 471 28J.5.1.3.4.1 Variation 1: Anthra 1,4 quinones as the Dienophiles 471 28.5.5.1.3.4.2 Variation 2: Anthracenetetrones as the Dienophiles 472 28.5.5.1.3.4.3 Variation 3: Anthradiquinone Epoxides as the Dienophiles 473 28J.5.1.3.4.4 Variation 4: 1,4 Dihydroxyanthra 9,10 quinone and Its 9 lmine as Dienophiles 474 28.5.5.1.3.4.5 Variation 5: Partially Hydrogenated or Bridged Anthra 9,10 quinones — 474 Table of Contents XXIX 28.5.5.1.3.5 Method 5: Diels Alder Reactions with Benzocyclobutenes as the Diene Precursors 475 28.5.5.1.3.6 Method 6: Diels Alder Reactions of Exocyclic Dienes and Exocyclic Vinylketene Acetals 476 28.5.5.1.3.7 Method 7: Strong Base Induced Cycloaddition of Homophthalic Anhydrides to Naphthoquinones 477 28.5.5.1.3.8 Method 8: Intramolecular Diels Alder Reactions 478 28.5.5.1.3.9 Method 9: Anionic Cyclization of Monoalkylanthra 9,10 quinones 479 28.5.5.1.3.9.1 Variation 1: Cyclization of Nitronatoanthra 9,10 quinones 479 28.5.5.1.3.9.2 Variation 2: Cyclization of 4 Hydroxy 2 (4 oxobutyl)anthra 9,10 quinone 480 28.5.5.1.3.10 Method 10: Anionic Cyclization of Dialkylanthra 9,10 quinones 481 28.5.5.1.3.10.1 Variation 1: Biomimetic Oxo Ester Cyclization 481 28.5.5.1.3.10.2 Variation 2: Lewis Acid Mediated Cyclization of ort/io Allyl Substituted Dioxolanyl Anthraquinones and Formylanthraquinones 482 28.5.5.1.3.10.3 Variation 3: Base Catalyzed Cyclization of a Nonsymmetrically Substituted 2,3 Diallylanthra 9,10 quinone 482 28.5.5.1.3.11 Method 11: 1,4 Dipolar Additions to Enones and Arynes 483 28.5.5.1.4 Synthesis of Anthraquinones Fused with Six Membered Rings: Tetraphene 7,12 diones 484 28.5.5.1.4.1 Method 1: Friedel Crafts Reactions 484 28.5.5.1.4.2 Method 2: Diels Alder Reactions 484 28.5.5.1.4.3 Method 3: Anionic Cyclizations 485 28.5.5.1.4.3.1 Variation 1: Cyclization of Monoalkylanthra 9,10 quinones 485 28.5.5.1.4.3.2 Variation 2: Cyclization of Dialkylanthra 9,10 quinones 486 28.5.5.1.4.4 Method4: [2 + 2 + 2] Cycloaddition 486 28.5.5.1.4.5 Method5: Rearrangement of Spiroanthracenediones 487 28.6 Product Class 6: Phenanthrene 9,10 diones, Stilbenequinones, Diphenoquinones, and Related Ring Assemblies A. M. Echavarren and S. Porcel 28.6 Product Class 6: Phenanthrene 9,10 diones, Stilbenequinones, Oiphenoquinones, and Related Ring Assemblies 507 28.6.1 Product Subclass 1: Phenanthrene 9,10 diones 507 28.6.1.1 Synthesis of Product Subclass 1 508 28.6.1.1.1 Method 1: Direct Oxidation of Polycyclic Arenes 508 28.6.1.1.1.1 Variation 1: Oxidation with Stoichiometric Oxidizing Reagents 508 28.6.1.1.1.2 Variation 2: Oxidation with Catalytic Oxidizing Reagents 511 28.6.1.1.2 Method 2: Ring Closure Reactions 512 28.6.1.1.2.1 Variation 1: Oxidative Biaryl Coupling of a Dicarbonyl Compounds 512 28.6.1.1.2.2 Variation 2: Photochemical Cyclization 513 28.6.1.1.2.3 Variation 3: Reductive Coupling of Carbonyls 516 28.6.1.2 Applications of Product Subclass 1 in Organic Synthesis 518 28.6.1.2.1 Method 1: Synthesis of Functionalized Fused Furans 518 XXX Table of Contents 28.6.1.2.2 Method 2: Catalyzed Epoxidation in the Presence of Phenanthrene 9,10 dione 519 28.6.1.2.3 Method 3: Synthesis of Heterocycles 519 28.6.1.2.4 Method 4: Synthesis of Biphenyl 2,2' dicarboxylic Acids 521 28.6.1.2.5 Method 5: Protection of 1,2 Diols 521 28.6.1.2.6 Method 6: Synthesis of Polycyclic Arenes via Bis Wittig Reactions 522 28.6.2 Product Subclass 2: Heterocyclic Analogues of Phenanthrene 9,10 diones 523 28.6.2.1 Synthesis of Product Subclass 2 524 28.6.2.1.1 Method 1: Oxidation of Hetarenes 524 28.6.2.1.1.1 Variation 1: Direct Oxidation of Hetarenes 524 28.6.2.1.1.2 Variation 2: Chlorination of Hetarenes 527 28.6.2.1.1.3 Variation 3: Oxidation of Hydroxy and/or Alkoxy Substituted Hetarenes with Strong Oxidants 528 28.6.2.1.1.4 Variation 4: Oxidation of Hydroxy and/or Alkoxy Substituted Hetarenes with Mild Oxidants 531 28.6.2.1.1.5 Variation 5: Oxidation of Amino Substituted Hetarenes 535 28.6.2.1.2 Method 2: Ring Closure Reactions 537 28.6.2.1.2.1 Variation 1: N—C Bond Forming Reactions 537 28.6.2.1.2.2 Variation 2: C—C Bond Forming Reactions 538 28.6.2 2 Applications of Product Subclass 2 in Organic Synthesis 539 28.6.2.2.1 Method 1: Oxidation of Functional Croups 539 28.6.3 Product Subclass 3: Stilbenequinones 541 28.6.3.1 Synthesis of Product Subclass 3 542 28.6.3.1.1 Method 1: Oxidation of Dihydroxystilbenes 543 28.6.3.1.2 Method 2: Oxidative Dimerization of Aromatic Compounds 544 28.6.3.1.2.1 Variation 1: Oxidation Dimerization of Phenols 544 28.6.3.1.2.2 Variation 2: Oxidative Dimerization of 2,4,6 Trimethylphenyl Chloroformate 547 28.6.3.2 Applications of Product Subclass 3 in Organic Synthesis 547 28.6.3.2.1 Method 1: Acid Catalyzed Rearrangement of Stilbenequinones 547 28.6.4 Product Subclass 4: Diphenoquinones 548 28.6.4.1 Synthesis of Product Subclass 4 550 28.6.4.1.1 Method 1: Oxidation of Biphenyldiols 550 28.6.4.1.2 Method 2: Oxidative Coupling of Phenols 551 28.6.4.1.2.1 Variation 1: Oxidative Coupling Using Stoichiometric Oxidants 551 28.6.4.1.2.2 Variation 2: Oxidative Coupling with Metal Catalysts 553 28.6.4.1.2.3 Variation 3: Enzymatic Oxidative Coupling 555 Table of Contents XXXI 28.7 Product Class 7: Hetarene Fused Quinones 28.7.1 Product Subclass 1: Nitrogen Containing Hetarene Quinones U. Pindur and T. Lemster 28.7.1 Product Subclass 1: Nitrogen Containing Hetarene Quinones 561 28.7.1.1 Synthesis of Product Subclass 1 561 28.7.1.1.1 Nitrogen Containing Hetarene p Quinones 561 28.7.1.1.1.1 Indolequinones, Carbazolequinones, and Higher Analogues 561 28.7.1.1.1.1.1 Method 1: Direct Oxidation of Hydroquinone Derivatives 562 28.7.1.1.1.1.2 Method 2: Ring Closure Reactions of Pyrroles 563 28.7.1.1.1.1.3 Method 3: Ring Closure Reactions of Substituted Benzoquinones 564 28.7.1.1.1.1.4 Method 4: Ring Expansion of Cyclobutenone Derivatives 566 28.7.1.1.1.2 Naphthindolizinequinones 567 28.7.1.1.1.2.1 Method 1: Ring Closure of 2 Pyridinium Substituted Naphtho 1,4 quinones with Nitromethane 567 28.7.1.1.1.3 Bispyrrolo Fused Quinones and Further Variants 568 28.7.1.1.1.3.1 Method 1: Cyclocondensation at Indolequinone 568 28.7.1.1.1.3.2 Method 2: Diels Alder Reaction with Indolequinones 569 28.7.1.1.1.3.3 Method 3: Double Cyclization of 2,5 Bis(arylamino) 3,6 dibromobenzo 1,4 quinones 570 28.7.1.1.1.4 Isoindolequinones 571 28.7.1.1.1.4.1 Method 1: o Dialkynylarene Annulation 571 28.7.1.1.1.4.2 Method 2: Azomethine 1,3 DipolarCycloaddition 572 28.7.1.1.1.5 Benzoxazolequinones 573 28.7.1.1.1.5.1 Method 1: Annulation of a Phenol Followed by Oxidation 573 28.7.1.1.1.6 Benzothiazolequinones 574 28.7.1.1.1.6.1 Method 1: Fremy's Salt Oxidation Followed by Nucleophilic Addition ¦¦¦ 574 28.7.1.1.1.7 Indazolequinones and Benzindazolequinones 576 28.7.1.1.1.7.1 Method 1: Ring Closure Reactions of Substituted Benzoquinones 576 28.7.1.1.1.7.2 Method 2: 1,3 DipolarCycloaddition Reactions with Quinones 577 28.7.1.1.1.8 Benzimidazolequinones 578 28.7.1.1.1.8.1 Method 1: Oxidation Reactions 578 28.7.1.1.1.9 Benzotriazolequinones 580 28.7.1.1.1.9.1 Method 1: 1,3 DipolarCycloaddition of p Quinones with Sodium Azide 580 28.7.1.1.1.10 Quinolinequinones, Isoquinolinequinones, and Higher Analogues 581 28.7.1.1.1.10.1 Method 1: Ring Closure Reactions of Substituted Benzoquinones 581 28.7.1.1.1.10.2 Method 2: Intramolecular Acid Catalyzed Cyclization of 2 [(2 Acetylaryl)amino]benzo 1,4 quinones 581 28.7.1.1.1.10.3 Method 3: Aza Diels Alder Reactions 582 XXXII Table of Contents 28.7.1.1.1.11 Isoquinolinequinones 583 28.7.1.1.1.11.1 Method 1: Oxidative Demethylation 583 28.7.1.1.1.11.2 Method 2: Ring Expansion of Cyclobutenone Derivatives Followed by Oxidation 584 28.7.1.1.1.12 Quinoxaline and Quinazolinequinones 585 28.7.1.1.1.12.1 Method 1: Oxidative Demethylation or Oxidation with Ammonium Cerium(IV) Nitrate 585 28.7.1.1.1.12.2 Method 2: Classical Annulation of 2,5 Dimethoxybenzaldehyde 587 28.7.1.1.2 Nitrogen Containing Hetarene o Quinones 587 28.7.1.1.2.1 Indolequinones 587 28.7.1.1.2.1.1 Method 1: Thermolysis of a 3 Azido 4 styrylbenzo 1,2 quinone 587 28.7.1.1.2.1.2 Method 2: Oxidation 588 28.7.1.1.2.2 o Quinones of Quinolines and Isoquinolines 588 28.7.1.1.2.2.1 Method 1: Fremy's Salt Oxidation 589 28.7.2 Product Subclass 2: Oxygen and Sulfur Containing Hetarene Quinones A. C. Criesbeck 28.7.2 Product Subclass 2: Oxygen and Sulfur Containing Hetarene Quinones 593 28.7.2.1 Synthesis of Product Subclass 2 594 28.7.2.1.1 Benzofuranquinones, Benzothiophenequinones, and Higher Annulated Analogues 594 28.7.2.1.1.1 Method 1: Oxidation of Benzofurans 595 28.7.2.1.1.1.1 Variation 1: Oxidation with Fremy's Salt 595 28.7.2.1.1.1.2 Variation 2: Oxidation with Chromium Reagents 597 28.7.2.1.1.1.3 Variation 3: Oxidation with Other Reagents 597 28.7.2.1.1.2 Method 2: Ring Closure Reactions of Furans 598 28.7.2.1.1.2.1 Variation 1: Furan Metalation and Cyclization 598 28.7.2.1.1.2.2 Variation 2: Fischer Carbene Reactions (Dotz Benzannulation) 598 28.7.2.1.1.2.3 Variation 3: Intramolecular Friedel Crafts Acylation 600 28.7.2.1.1.3 Method 3: Ring Closure Reactions of Quinones 601 28.7.2.1.1.3.1 Variation 1: Ullmann Reaction of Benzoquinones 601 28.7.2.1.1.3.2 Variation 2: Dehydration of Hydroxylated Quinones 601 28.7.2.1.1.3.3 Variation 3: Nucleophilic Addition of Hydroxyaryl Substituted Quinones 602 28.7.2.1.1.3.4 Variation 4: Intramolecular Nucleophilic Substitution 602 28.7.2.1.1.3.5 Variation 5: Oxidative Cyclization by Mercury(ll) Acetate and 3 Chloroperoxybenzoic Acid 603 28.7.2.1.1.4 Method 4: Ring Annulation of Quinones 604 28.7.2.1.1.4.1 Variation 1: Michael Addition and Subsequent Cyclization of CH Active Methylene Compounds 604 28.7.2.1.1.4.2 Variation 2: Michael Addition and Subsequent Cyclization of Phenols — 604 28.7.2.1.1.4.3 Variation 3: Addition of Enamines and Vinyl Sulfides 605 Table of Contents XXXIII 28.7.2.1.1.4.4 Variation 4: Photochemical Addition of Alkenes and Alkynes to Quinones 606 28.7.2.1.1.4.5 Variation 5: Palladium Catalyzed Coupling and Ring Closure of Phenyliodonium Betaines 607 28.7.2.1.1.4.6 Variation 6: Diels Alder Cycloaddition 607 28.7.2.1.1.5 Method 5: Ring Closure Reactions of Bi(quinones) 608 28.7.2.1.1.5.1 Variation 1: Acid and Base Induced Ring Closure 608 28.7.2.1.1.5.2 Variation 2: Thermal and Photochemical Ring Closure 609 28.7.2.1.1.6 Method 6: Ring Enlargement of Cyclobutenones 609 28.7.2.1.1.7 Method 7: Modification of Benzo[b]furanquinones 611 28.7.2.1.1.7.1 Variation 1: Diels Alder Reactions 611 28.7.2.1.1.7.2 Variation 2: Hetero Diels Alder Reactions 613 28.7.2.1.1.7.3 Variation 3: Palladium Catalyzed Coupling of Boronates 613 28.7.2.1.2 Benzo[c]furanquinones 614 28.7.2.1.3 Pyranbenzoquinones and Pyrannaphthoquinones 614 28.7.2.1.4 Benzothiophenequinones 614 28.7.2.1.4.1 Method 1: Oxidation of Benzo[b]thiophene Derivatives 615 28.7.2.1.4.2 Method 2: Intramolecular Condensation of Thiophenecarboxylates 615 28.7.2.1.4.2.1 Variation 1: Using Thiophenecarboxylates 615 28.7.2.1.4.2.2 Variation 2: Using Benzoic Acid Derivatives 616 28.7.2.1.4.3 Method 3: Thiophene Metalation and Tandem Nucleophilic Addition ¦•¦ 616 28.7.2.1.4.4 Method 4: Tandem Conjugate Addition and Cyclization 616 28.7.2.1.4.5 Method 5: Intra and Intermolecular Friedel Crafts Acylations 617 28.8 Product Class 8: Sulfur Analogues of Quinones M. Yoshifuji and S. Kawasaki 28.8 Product Class 8: Sulfur Analogues of Quinones 623 28.8.1 Product Subclass 1: p Monothioquinones 623 28.8.1.1 Synthesis of Product Subclass 1 623 28.8.2 Product Subclass 2: o Monothioquinones 626 28.8.21 Synthesis of Product Subclass 2 626 28.8.3 Product Subclass 3: Dithioquinones 627 28*3.1 Synthesis of Product Subclass 3 627 28.9 Product Class 9: Benzo 1,2 , Benzo 1,4 , Naphtho 1,2 , and Naphtho 1,4 quinone Imines and Diimines M. C. Carrefio and M. Ribagorda 28.9 Product Class 9: Benzo 1,2 , Benzo 1,4 , Naphtho 1,2 , and Naphtho 1,4 quinone Imines and Diimines 629 28.9.1 Product Subclass 1: Benzoquinone Imines and Diimines 630 28^.1.1 Synthesis of Product Subclass 1 630 28.9.1.1.1 Method 1: Oxidation of Anilines and Benzenediamines 630 XXXIV Table of Contents 28.9.1.1.1.1 Variation 1: Using Lead(IV) Acetate 630 28.9.1.1.1.2 Variation 2: Using Hypohalites 635 28.9.1.1.1.3 Variation 3: Using Silver(l) Oxide 638 28.9.1.1.1.4 Variation 4: Using Iron(lll) Chloride 640 28.9.1.1.1.5 Variation 5: Using Manganese(IV) Oxide 642 28.9.1.1.1.6 Variation 6: Using Hypervalent Iodine Reagents 644 28.9.1.1.1.7 Variation 7: Using Peroxides 645 28.9.1.1.1.8 Variation 8: Using Cobalt Mediated Catalytic Oxidation by Oxygen 646 283.1.1.1.9 Variation 9: Using Fremy's Salt 647 28.9.1.1.1.10 Variation 10: Using Ammonium Cerium(IV) Nitrate 647 28.9.1.1.1.11 Variation 11: Oxidative Coupling of Phenols and Anilines with Amines — 647 28.9.1.1.1.12 Variation 12: Electrooxidation 649 28.9.1.1.2 Method 2: Condensation of Quinone Derivatives with Amines 658 28.9.1.1.2.1 Variation 1: Intermolecular Processes 658 28.9.1.1.2.2 Variation 2: Intramolecular Processes 663 28.9.1.1.3 Method 3: Transition Metal Quinone Diimine Synthesis 667 28.9.1.1.4 Method 4: Organometallic C—N Coupling from N Chloroquinone Imines 669 283.1.2 Applications of Product Subclass 1 in Organic Synthesis 670 28.9.1.2.1 Method 1: Diels Alder Reactions 670 28.9.1.2.1.1 Variation 1: Cycloaddition Reactions of Benzo 1,2 quinone Imines 670 28.9.1.2.1.2 Variation 2: Cycloaddition Reactions of Benzo 1,4 quinone Imines 673 28.9.1.2.2 Method 2: Dipolar Cycloadditions 681 283.1.2.3 Method 3: Reactions with Alkenes Promoted by Lewis Acids 682 28.9.1.2.4 Method 4: 1,4 Addition Reactions 695 28.9.2 Product Subclass 2: Naphthoquinone Imines and Diimines 706 28.9.2.1 Synthesis of Product Subclass 2 706 28.9.2.1.1 Method 1: Oxidative Coupling of Naphthols with Amines 706 28.9.2.1.2 Method 2: Oxidative Coupling of 1 Naphthylcyanamide with Anilines ••• 710 28.9.2.1.3 Method 3: Substitutions on Naphthoquinones with Amines 712 283.2.1.3.1 Variation 1: Substitution of Sulfonic Groups 712 28.9.2.1.3.2 Variation 2: Substitution of Methoxy Groups 714 283.2.1.4 Method 4: Condensation of Naphthoquinones with Amines 714 28.9.2.1.5 Method 5: Condensation of Naphthoquinones with /V Sulfinylarylamines 716 283.2.1.6 Method 6: Reactions of Naphthoquinones with N Phenyliminophosphoranes 717 283.2.1.7 Method 7: Oxidation of Aminonaphthols, Naphthalenediamines, and Naphthylamines 718 283.2.1.8 Method 8: Diels Alder Reactions of Isoindoles with Activated Acetylene Derivatives 721 283.2.1.9 Method 9: Synthesis and Oxidation of N Hydroxy N phenyl naphthalen 1 amines 722 283.2.1.10 Method 10: Reactions of Naphthoquinones with Bis(trimethylsilyl)carbodiimide 723 283.2.2 Applications of Product Subclass 2 in Organic Synthesis 724 283.2.2.1 Method 1: Halogenation 724 283.2.2.2 Method 2: [3 + 2] Photoaddition with Alkenes 726 Table of Contents XXXV 28.9.2.2.3 Method 3: 1,4 Addition Aromatization 726 28.9.2.2.4 Method 4: Oxidative Coupling 729 28.9.2.2.5 Method 5: The Imino Group as Nucleophile 729 28.10 Product Class 10: Anthraquinone and Phenanthrenedione Imines and Diimines C. Avendano and J. C. Menendez 28.10 Product Class 10: Anthraquinone and Phenanthrenedione Imines and Diimines 735 28.10.1 Product Subclass 1:Anthra 9,10 quinone Imines and Diimines 739 28.io.li Synthesis of Product Subclass 1 739 28.10.1.1.1 Ring Annulation or Ring Closure Reactions 739 28.10.1.1.1.1 Method 1: Diels Alder Reactions of Naphthoquinone Imines 739 28.10.1.1.1.2 Method 2: Oxidative Photochemical Cyclization of 9 (2 lodoanilino) 4,5 phenanthrolin 10 ols 740 28.10.1.1.1.3 Method 3: Intramolecular Friedel Crafts Acylation of 1 (2 Carboxyphenyl)isoquinolines 741 28.10.1.1.1.4 Method 4: Intramolecular Friedel Crafts Acylation of 10 Hetaryl 2,9 phenanthridine 1 carbonitriles 741 28.10.1.1.1.5 Method 5: Intramolecular Cyclization of 2,2' Bis(phthalimido)biphenyls 742 28.10.1.1.1.6 Method 6: Double Cyclization of 3 [(2 Arylethyl)amino] benzo[c]furan 1(3H) one 743 28.10.1.1.1.7 Method 7: Hydrolytic Cyclization of N (3 {2 [(5,8 Dioxo 5,8 dihydro quinolin 6 yl)amino]phenyl} 3 oxopropyl) 2,2,2 trifluoro acetamide 744 28.10.1.1.2 Creation of the Quinone Imine Functionality on a Preexisting Six Membered Ring 745 28.10.1.1.2.1 Method 1: Oxidation of N Arylanthracen 9 amines, Tetracen 5 amines, or Azaviolanthrenes 745 28.10.1.1.2.2 Method 2: Photonitrosation of 9 Anthrol 748 28.10.1.1.2.3 Method 3: Palladium Catalyzed Amination/Oxidation of 9 Bromoanthracenes 749 28.10.1.1.2.4 Method 4: Oxidative Amination of 9 Anthrones 750 28.10.1.1.2.5 Method 5: Oxidation of 10 Amino 9 anthrols 750 28.10.1.1.2.6 Method 6: Condensation of 9 Anthrones with Nitrosoarenes 751 28.10.1.1.2.7 Method 7: Reactions of 10,10 Dibromo 9 anthrones with Nitrogen Containing Nucleophiles 752 28.10.1.1.2.8 Method 8: Nitrosation of Anthracen 9 amine 752 28.10.1.1.2.9 Method 9: Diazocoupling of 9 Anthrones 753 28.10.1.1.2.10 Method 10: Decomposition of 10 Azido 9 anthrones 754 28.10.1.1.2.11 Method 11: Condensation of Anthra 9,10 quinones or Anthra 9,10 quinone Acetals with Ammonia or Amines 754 28.10.1.1.2.12 Method 12: Condensation of 1 Aminoanthra 9,10 quinones with Amides, Amidines, or Nitriles 756 XXXVI Table of Contents 28.10.1.1.2.13 Method 13: Intramolecular Condensations of Anthra 9,10 quinones with Masked Amino Croups 757 28.10.1.1.2.14 Method 14: Reactionsof Anthra 9,10 quinones with Aryliminodimagnesium Reagents 759 28.10.1.1.2.15 Method 15: Reactions of Anthraquinones with Bis(trimethylsilyl)carbodiimide 760 28.10.1.1.2.16 Method 16: Intramolecular Cyclization of 1 (Cyanomethyl) or 1 (Carbamoylmethyl)anthra 9,10 quinones 761 28.10.1.1.2.17 Method 17: Reactions of 9 Aryloxyanthra 1,10 quinones with Amines ••• 761 28.10.1.1.2.18 Method 18: Reactionsof 1 [2 (Dimethylamino)vinyl]azanthraquinones with Ammonia 762 28.10.1.1.2.19 Method 19: Self Coupling of 1 Aminoanthra 9,10 quinones 763 28.10.1.1.2.20 Method 20: Reactions of 1 Substituted Anthra 9,10 quinones with Nucleophiles 764 28.10.1.1.2.20.1 Variation 1: Reactionsof 1 Haloanthra 9,10 quinones with Hydrazine or 2 Aminobenzenethiol 764 28.10.1.1.2.20.2 Variation 2: Reactionsof 1 Alk 1 ynylanthra 9,10 quinoneswith Hydrazines 765 28.10.1.1.2.21 Method 21: Copper Catalyzed Reactions of 1 Haloanthra 9,10 quinones with Amidines, Guanidines, and Related Compounds 766 28.10.1.1.2.22 Method 22: Synthesis from Anthracenes and Anthracene Diones Bearing a Nitrogen Containing Croup or Groups 767 28.10.1.1.2.22.1 Variation 1: Hydrolysis of Anthra 9,10 quinone Diimines to Monoimines 767 28.10.1.1.2.22.2 Variation 2: Dipolar Cycloadditions between Quinomethanes and Azides, and Diazoalkane Extrusion 768 28.10.1.1.2.22.3 Variation 3: Transformations of Anthra 9,10 quinone Imines and Hydrazones 769 28.10.1.1.2.22.4 Variation 4: Transformations of Anthra 9,10 quinone Oximes 769 28.10.1.1.2.22.5 Variation 5: Reactionsof 10 Diazoanthracen 9(10H) ones with Nitrogen Containing Electrophiles 770 28.10.1.1.2.22.6 Variation 6: ReductiveTautomerization of Anthra 1,4 quinone Imines ••¦ 771 28.10.2 Product Subclass 2: Anthra 1,2 quinone and Anthra 1,4 quinone Imines and Diimines 771 28.10.21 Synthesis of Product Subclass 2 771 28.10.2.1.1 Ring Closure Reactions 771 28.10.2.1.1.1 Method 1: Oxidative Coupling of 1 Phenyl 2,3 bis(pyrimidin 5 yl) benzenes 771 28.10.2.1.1.2 Method 2: Cycloaddition of Homophthalic Anhydrides and Benzo 1,4 quinone Imines and Subsequent Oxidation 772 28.10.2.1.2 Creation of the Quinone Imine Functionality on a Preexisting Six Membered Ring 774 28.10.2.1.2.1 Method 1: Oxidation of 1 (Acylamino) 2 anthrols 774 28.10.2.1.2.2 Method 2: Oxidation of Anthracenamines and Their Derivatives 774 28.10.2.1.2.3 Method 3: Rearrangement of 4 Aryloxyanthracen 1 amines and Related Compounds 775 Table of Contents XXXVII 28.10.2.1.2.4 Method 4: Condensation of Anthra 9,10 quinone Diamines and Anthracenamines with Carbonyl Compounds 777 28.10.2.1.2.5 Method 5: Condensation of Anthra 1,2 quinones with Hydrazines 778 28.10.3 Product Subclass 3: Phenanthrene 9,10 dione Imines and Diimines 779 28.io.3i Synthesis of Product Subclass 3 779 28.10.3.1.1 Ring Closure Reactions 779 28.10.3.1.1.1 Method 1: Transannular Cyclizations of [22]Metacyclophanes with N Bromosuccinimide 780 28.10.3.1.1.2 Method 2: Metal Induced Oxidative Intramolecular Aryl Aryl Coupling 780 28.10.3.1.1.3 Method 3: Synthesis of Oxoaporphine Alkaloids by Aryl Aryl Coupling 782 28.10.3.1.1.4 Method 4: PschorrCyclization of 1 (2 Aminobenzyl)isoquinolines 784 28.10.3.1.1.5 Method 5: Oxidative Cyclization of Bisarylhydrazones 785 28.10.31 2 Creation of the Quinone Imine Functionality on a Preexisting Six Membered Ring 787 28.10.3.1.2.1 Method 1: Reaction of Phenanthrene 9,10 diones with Nucleophiles ••• 787 28.10.3.1.2.1.1 Variationi: Reactions with 1,2 Diamines 787 28.10.3.1.2.1.2 Variation 2: Condensation of Phenanthrene 9,10 diones with Hydroxylamine or Sodium Hexamethyldisilazanide 789 28.10.3.1.2.1.3 Variation 3: Condensation of Phenanthrene 9,10 diones with Imino hydrazides, Sulfanamide, Thiosemicarbazide, Semicarbazide, or Aminoguanidines 790 28.10.3.1.2.1.4 Variation 4: Condensation of Phenanthrene 9,10 diones with S Alkylisothiosemicarbazides and Related Compounds 791 28.10.3.1.2.1.5 Variation 5: Reductive Condensation of Phenanthrene 9,10 diones with Aromatic Nitroso or Nitro Compounds 793 28.10.3.1.2.2 Method 2: Condensation of Phenanthrene 9,10 diamines with a Dicarbonyl Compounds 793 28.10.3.1.2.3 Method 3: Condensation of Phenanthrene 9,10 diamines with Bis(methyloximes) 794 28.10.3.1.2.4 Method 4: Reactions of Phenanthrene 9,10 diamines with a Nitro Ketones 795 28.10.3.1.2.5 Method 5: Condensation of Phenanthrene 3,9 diones with 1,2 Diamines 796 28.10.3.1.2.6 Method 6: Condensation of 9 Nitrophenanthrenes with Anilines 797 28.10.3.1.2.7 Method 7: Condensation of lminophenanthren 9(10H) ones with Amines 797 28.10.3.1.2.8 Method 8: Reaction of Phenanthrene 9,10 diones with Arsinimines 798 28.10.3.1.2.9 Method 9: Condensation of Phenanthrene 9,10 dione Monooxime with 1,1 Diarylalkenes 799 28.10.3.1.2.10 Method 10: Condensation of Phenanthrene 9,10 dione Diimines or Dioximeswithgem Dihalides 800 28.10.3.1.2.11 Method 11: Reaction of Phenanthrene with Trithiazyl Trichloride 801 28.10.3.1.2.12 Method 12: Ring Expansion of Phenanthro[9,10 d][1,2,3]triazoles or Phenanthro[9,10 c][1,2,5]oxadiazoles 801 XXXVIII Table of Contents _ 28.11 Product Class 11: Quinone Diazides A. C. Griesbeck and E. Zimmermann 28.11 Product Class 11: Quinone Diazides 807 28.11.1 Synthesis of Product Class 11 809 28.11.1.1 Method 1: Diazotization of Amino Substituted Aromatic Alcohols 810 28.11.1.1.1 Variation 1: Diazotization in Aqueous Media 810 28.11.1.1.2 Variation 2: Diazotization in Organic Solvents 812 28.11.1.1.3 Variation 3: Nitration of Substituted Anilines 816 28.11.1.2 Method 2: Aromatic Substitution of Diazonium Salts 818 28.11.1.2.1 Variation 1: Hydrolysis of 2 or 4 Substituted Diazonium Salts 818 28.11.1.2.2 Variation 2: Elimination of HX from Diazonium Salts 819 28.11.1.2.3 Variation 3: Aromatic Substitution of Aryl Fluorides 820 28.11.1.3 Method 3: Oxidation of Arenediazonium Cations 821 28.11.1.4 Method 4: o or p Nitrosylation of Phenols 821 28.11.1.5 Method 5: Formation of Tosylhydrazones from Quinones 822 28.11.1 6 Method 6: Electrophilic Substitution of Quinone Diazides 823 28.11.1.7 Method 7: Diazo Croup Transfer Reactions 823 28.11.1.8 Methods 8: Additional Methods 825 28.11.2 Applications of Product Class 11 in Organic Synthesis 825 28.11.2.1 Method 1: The Sus Reaction 825 28.11.2.2 Method 2: Application in Photolithographic Processes 827 28.12 Product Class 12: Quinomethanes 28.12.1 Product Subclass 1: o Quinomethanes T. R. R. Pettus and C. Selenski 28.12.1 Product Subclass 1: o Quinomethanes 831 28.12.11 Synthesis of Product Subclass 1 835 28.12.1.1.1 Quinone Enolization 835 28.12.1.1.1.1 Methodi: Heat Assisted Quinone Enolization 835 28.12.1.1.1.2 Method 2: Base Assisted Quinone Enolization 836 28.12.1.1.1.2.1 Variation 1: Using Lithium Methoxide 836 28.12.1.1.1.2.2 Variation 2: Using Sodium Methanethiolate 837 28.12.1.1.1.2.3 Variation 3: Using Amines 838 28.12.1.1.1.3 Method 3: Photochemically Assisted Quinone Enolization 839 28.12.1.1.2 Oxidation 840 28.12.1.1.2.1 Methodi: Oxidation Using Silver(l) Oxide 840 28.12.1.1.3 Extrusions and Retrocycloadditions 843 28.12.1.1.3.1 Method 1: Nucleophilic Displacement 843 28.12.1.1.3.2 Method 2: Mannich Base Precursors 843 Table of Contents XXXIX 28.12.1.1.3.2.1 Variation 1: Thermal Induction 844 28.12.1.1.3.2.2 Variation 2: Quaternization 846 28.12.1.1.3.3 Method 3: 2 (1H Benzotriazol 1 ylmethyl)phenol Precursors 847 28.12.1.1.3.3.1 Variation 1: Basic Conditions 848 28.12.1.1.3.3.2 Variation 2: Thermal Conditions 849 28.12.1.1.3.4 Method 4: 4H 1,2 Benzoxazine Precursors (Thermal Extrusion) 851 28.12.1.1.3.5 Method 5: 2 (fert Butoxycarbonyloxy)benzaldehyde and 2 (tert Butoxy carbonyloxy)benzyl Alcohol Precursors (Basic Conditions) ¦•• 852 28.12.1.1.3.6 Method 6: 2 (Hydroxymethyl)phenol Precursors 858 28.12.1.1.3.6.1 Variation 1: Thermal Induction 858 28.12.1.1.3.6.2 Variation 2: Derivatization of the 2 (Hydroxymethyl)phenol Precursor ••¦ 860 28.12.1.1.3.6.3 Variation 3: Photochemical Induction 860 28.12.1.1.3.6.4 Variation 4: Lewis Acid Induction 861 28.12.1.1.3.6.5 Variation 5: Lewis Base Induction 862 28.12.1.1.3.7 Method 7: 2 Phenylbenzodioxaborin Precursors 863 28.12.1.1.3.7.1 Variation 1: Lewis Acid Induction 864 28.12.1.1.3.8 Method 8: 2 (Halomethyl)phenol Precursors 866 28.12.1.1.3.8.1 Variation 1: Neutral Conditions 867 28.12.1.1.3.8.2 Variation 2: Basic Conditions 867 28.12.1.1.3.8.3 Variation 3: Lewis Acidic Conditions 868 28.12.2 Product Subclass 2: p Quinomethanes A. G. Griesbeck 28.12.2 Product Subclass 2: p Quinomethanes 873 28.i2.2i Synthesis of Product Subclass 2 874 28.12.2.1.1 Method 1: Oxidation of 4 Substituted Phenols 876 28.12.2.1.1.1 Variation 1: Using Silver(l), Lead(IV), or Manganese(IV) Oxide 876 28.12.2.1.1.2 Variation 2: Using Potassium Hexacyanoferrate(lll) 877 28.12.2.1.1.3 Variation 3: Using Other Oxidants 877 28.12.2.1.2 Method 2: Dehydration of 4 (Hydroxyalkyl) and 4 (Hydroxyalkyl)phenyl Substituted Phenols 879 28.12.2.1.2.1 Variation 1: Thermal Dehydration of 4 (Hydroxyalkyl) Substituted Phenols 879 28.12.2.1.2.2 Variation 2: Acid Catalyzed Dehydration of 4 (Hydroxyalkyl) Substituted Phenols 879 28.12.2.1.2.3 Variation 3: Dehydration of 4 (Hydroxyalkyl) Substituted Phenols Using Lithium Aluminum Hydride 879 28.12.2.1.3 Method 3: Dehydrohalogenation of 4 Halomethyl Substituted Phenols 880 28.12.2.1.3.1 Variation 1: Using Amine Bases 880 28.12.2.1.3.2 Variation 2: Using Weak Bases in Aqueous Media 881 28.12.2.1.3.3 Variation 3: Using Metal Alkoxides 881 28.12.2.1.4 Method 4: Acid Catalyzed Dehydration of 4 Methoxyphenyl Substituted Alcohols 882 28.12.2.1.5 Method 5: Elimination of Chloromethane from 4 Chloroalkyl Substituted Anisoles 882 28.12.2.1.6 Method 6: Acid Elimination from 4 (Acyloxy)alkyl Substituted Phenols 883 XL Table of Contents 28.12.2.1.7 Method 7: Decomplexation of Quinomethanes from re Palladium Complexes 884 28.12.2 1.8 Method 8: Condensation of Phenols with Alkyl or Acyl Halides 884 28.12.2.1.8.1 Variation 1: Thermal Condensation 885 28.12.2.1.8.2 Variation 2: Lewis Acid Catalyzed Condensation 885 28.12.2.1.9 Method 9: Reaction of Phenols with Carbenium Ions 885 28.i2.2i.io Method 10: Reaction of Aryl Carbanions with Carbonyl Compounds — 886 28.12.2.1.10.1 Variation 1: Reaction of Metalated Phenols with Carbonyl Compounds 886 28.12.2.1.10.2 Variation 2: Reaction of Metalated Arenes with 4 Acylphenols 887 28.12.2.1.11 Method 11: Oxidation of Phenols to p Diphenoquinones 888 28.12.2.1.12 Method 12: Ring Closure Reactions 888 28.12.2.1.13 Method 13: Addition of Nudeophiles to o Quinones 889 28.12.2.1.14 Method 14: Addition of Nudeophiles to p Quinones 890 28.i2.2i.i5 Method 15: Knoevenagel Addition to p Quinones 890 28.12.2.1.16 Method 16: Wittig Reaction of p Quinones 891 28.12.2.1.17 Method 17: Ketene Additions to p Quinones 893 28.i2.2i.i8 Method 18: Photochemical Addition of Alkynes to p Quinones 893 28.12.2.1.19 Method 19: Modification of p Quinomethanes 894 28.12.2.1.20 Method 20: Condensation of Carbonyl Compounds with Anthrones — 894 28.12.2.1.21 Method 21: Oxidation of Nitrobenzylic Carbanions 895 Keyword Index 901 Author Index 949 Abbreviations 1001
adam_txt	^^^^.^ _™™_ XIII Table of Contents Introduction A. G. Griesbeck Introduction 1 28.1 Product Class 1: Benzo 1,4 quinones 28.1.1 Product Subclass 1: Metal Substituted Benzo 1,4 quinones B. G. Vong and E. A. Theodorakis 28.1.1 Product Subclass 1: Metal Substituted Benzo 1,4 quinones 13 28.1.1.1 Synthesis of Product Subclass 1 14 28.1.1.1.1 Method 1: Tin Substituted Benzo 1,4 quinones by Cyclobutenone Ring Expansion 14 28.1.1.1.2 Method 2: Tin Substituted Benzo 1,4 quinones by Stannylation of Benzo 1,4 quinones 16 28.1.1.1.3 Method 3: Silicon Substituted Benzo 1,4 quinones by Reaction of Organolithium Species 16 28.1.1.1.4 Method 4: Silicon Substituted Benzo 1,4 quinones by Cyclobutenone Ring Expansion 17 28.1.1.1.5 Method 5: Silicon Substituted Benzo 1,4 quinones by Carbene Annulation 20 28.1.1.1.6 Method 6: Silicon Substituted Benzo 1,4 quinones by Nucleophilic Substitution 21 28.1.1.1.7 Method 7: Boron Substituted Benzo 1,4 quinones by Carbene Benzannulation 22 28.1.1.2 Applications of Product Subclass 1 in Organic Synthesis 22 28.1.1.2.1 Method 1: Palladium Catalyzed Cross Coupling Reactions of Tin Substituted Benzo 1,4 quinones 22 28.1.1.2.1.1 Variation 1: Allylation 23 28.1.1.2.1.2 Variation 2: Coupling with Aromatic and Heteroaromatic Iodides 23 28.1.1.2.1.3 Variation 3: Oxidative Dimerization 25 28.1.1.2.1.4 Variation 4: Benzannulation 26 28.1.1.2.2 Method 2: Silicon/Halide Exchange Reactions of Silicon Substituted Benzo 1,4 quinones 27 28.1.1.2.3 Method 3: Oxidation of the Boron Substituent in Boron Substituted Benzo 1,4 quinones 28 XIV Table of Contents 28.1.2 Product Subclass 2: Halogen Substituted Benzo 1,4 quinones M. Balci, M. Celik, and M. S. Gultekin 28.1.2 Product Subclass 2: Halogen Substituted Benzo 1,4 quinones 31 28.1.2.1 Monohalobenzo 1,4 quinones 31 28.1.2.1.1 Synthesis of Monohalobenzo 1,4 quinones 31 28.1.2.1.1.1 Method 1: Oxidation of 4 Amino 3 iodophenol Using Potassium Dichromate 31 28.1.2.1.1.2 Method 2: Oxidation of 1,4 Hydroquinones with Persulfate or Ammonium Cerium(IV) Nitrate 32 28.1.2.1.1.3 Method 3: Oxidation of 1,4 Hydroquinones Catalyzed by an Oxovanadium Complex 34 28.1.2.1.1.4 Method 4: Oxidation of 1,4 Hydroquinones Catalyzed by Caseous Nitrogen Oxides 34 28.1.2.1.1.5 Methods 5: Miscellaneous Oxidations of Anilines and 1,4 Hydroquinones 35 28.1.2.1.2 Applications of Monohalobenzo 1,4 quinones in Organic Synthesis 35 28.1.2.2 2,3 Dihalobenzo 1,4 quinones 39 28.1.2.2.1 Synthesis of 2,3 Dihalobenzo 1,4 quinones 39 28.1.2.2.1.1 Methodi: Halogenation of Benzo 1,4 quinone 39 28.1.2.2.1.2 Method 2: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate 41 28.1.2.2.2 Applications of 2,3 Dihalobenzo 1,4 quinones in Organic Synthesis 41 28.1.2.3 2,5 Dihalobenzo 1,4 quinones 42 28.1.2.3.1 Synthesis of 2,5 Dihalobenzo 1,4 quinones 42 28.1.2.3.1.1 Methodi: Oxidation of 1,2,4,5 Tetrafluorobenzene 42 28.1.2.3.1.2 Method 2: Oxidation of 1,4 Hydroquinones 43 28.1.2.3.1.3 Method 3: Oxidative Demethylation of 1,4 Dimethoxybenzenes 43 28.1.2.4 2,6 Dihalobenzo 1,4 quinones 43 28.1.2.4.1 Synthesis of 2,6 Dihalobenzo 1,4 quinones 43 28.1.2.4.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones Catalyzed by Metalated Phthalocyanines 43 28.1.2.4.1.2 Method 2: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate 44 28.1.2.4.1.3 Method 3: Oxidation of Phenols Using Metal Oxides 44 28.1.2.4.2 Applications of 2,6 Dihalobenzo 1,4 quinones in Organic Synthesis 45 28.1.2.5 2,3,5 Trihalobenzo 1,4 quinones 46 28.1.2.5.1 Synthesis of 2,3,5 Trihalobenzo 1,4 quinones 46 28.1.2.5.1.1 Methodi: Halogenation of Benzo 1,4 quinones 46 28.1.2.5.1.2 Method 2: Bromination of 2,5 Dichlorobenzo 1,4 quinone 46 28.1.2.5.1.3 Method 3: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate 47 28.1.2.5.2 Applications of 2,3,5 Trihalobenzo 1,4 quinones in Organic Synthesis 47 Table of Contents XV 28.1.2.6 2,3.5,6 Tetrahalobenzo 1,4 quinones 48 28.1.2.6.1 Synthesis of 2,3,5,6 Tetrahalobenzo 1,4 quinones 48 28.1.2.6.1.1 Method 1: Halogenation of Benzo 1,4 quinone 48 28.1.2.6.1.2 Method 2: Oxidation of 1,4 Hydroquinones Using Hydrogen Peroxide or Chlorine 49 28.1.2.6.1.3 Method 3: Oxidation of a 1,4 Hydroquinone Using Ammonium Cerium(IV) Nitrate, and Other Reactions 49 28.1.2.6.2 Applications of 2,3,5,6 Tetrahalobenzo 1,4 quinones in Organic Synthesis — 49 28.1.3 Product Subclass 3: Chalcogen Substituted Benzo 1,4 quinones S. H. Kim and E. A. Theodorakis 28.1.3 Product Subclass 3: Chalcogen Substituted Benzo 1,4 quinones 53 28.1.3.1 Synthesis of Product Subclass 3 54 28.1.3.1.1 Method 1: Oxidative Dearomatization 54 28.1.3.1.1.1 Variation 1: Oxidation of Chalcogen Substituted Phenols 54 28.1.3.1.1.2 Variation 2: Oxidation of Chalcogen Substituted Hydroquinones 56 28.1.3.1.1.3 Variation 3: Oxidative Demethylation of Chalcogen Substituted Hydroquinone Mono and Diethers 57 28.1.3.1.1.4 Variation 4: Miscellaneous Oxidations 58 28.1.3.1.2 Method 2: Nucleophilic Additions on the Benzoquinone Motif 59 28.1.3.1.2.1 Variation 1: Conjugate Addition/Oxidation 59 28.1.3.1.2.2 Variation 2: Conjugate Addition Elimination 61 28.1.3.1.3 Method 3: Ring Expansion of Cyclobutenediones 61 28.1.3.2 Applications of Product Subclass 3 in Organic Synthesis 64 28.1.3.2.1 Method 1: Cycloaddition Reactions of Chalcogen Substituted Benzo 1,4 quinones 64 28.1.3.2.2 Method 2: Conjugate Additions of Chalcogen Substituted Benzo 1,4 quinones 66 28.1.4 Product Subclass 4: Nitrogen and Phosphorus Substituted Benzo 1,4 quinones H. Lee and E. A. Theodorakis 28.1.4 Product Subclass 4: Nitrogen and Phosphorus Substituted Benzo 1,4 quinones 71 28.1.4.1 Synthesis of Product Subclass 4 71 28.1.4.1.1 Method 1: Nitrogen Substituted Benzo 1,4 quinones by Nucleophilic Addition/Oxidation 71 28.1.4.1.2 Method 2: Nitrogen Substituted Benzo 1,4 quinones by Nucleophilic Substitution 74 28.1.4.1.3 Method 3: Nitrogen Substituted Benzo 1,4 quinones by Oxidation of a Benzene Ring 75 XVI Table of Contents 28.1.4.1.4 Method 4: Phosphorus Substituted Benzo 1,4 quinones by Addition/Elimination and Addition/Oxidation Sequences — 76 28.1.4.2 Applications of Product Subclass 4 in Organic Synthesis 77 28.1.4.2.1 Method 1: Ring Contraction of Benzoquinones 77 28.1.4.2.1.1 Variation 1: Synthesis of Cyclopentenediones from Azidoquinones 77 28.1.4.2.1.2 Variation 2: Synthesis of Butenolides from Azidoquinones 78 28.1.4.2.1.3 Variation 3: Cyanoketenes from Aminoquinones and Their Use in Synthesis 79 28.1.4.2.2 Method 2: Formation of Oxazoles 80 28.1.4.2.3 Method 3: Synthesis of Hetarene Fused Benzo 1,4 quinones 82 28.1.5 Product Subclass 5: Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Heteroatoms M. Balci, M. Celik, and M. S. Cultekin 28.1.5 Product Subclass 5: Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Heteroatoms 87 28.1.5.1 Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Halogens 87 28.1.5.1.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Halogens 88 28.1.5.1.1.1 Method 1: Oxidation of Phenols with Chlorous Acid 88 28.1.5.1.1.2 Method 2: Oxidation of Phenols with Manganese(IV) Oxide 88 28.1.5.1.1.3 Method 3: Oxidative Demethylation of Dimethoxybenzenes 89 28.1.5.1.1.4 Method 4: Oxidative Debenzylation of Bis(benzyloxy)benzenes 90 28.1.5.2 Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Oxygen 91 28.1.5.2.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Oxygen 92 28.1.5.2.1.1 Method 1: Oxidation of Hydroquinones with Ammonium Cerium(IV) Salts 92 28.1.5.2.1.2 Method 2: Oxidation of Hydroquinones with Silver(ll) Oxide 93 28.1.5.2.1.3 Method 3: Oxidation of Hydroquinones with Polymer Supported (Diacetoxyiodo)benzene 94 28.1.5.2.1.4 Method 4: Oxidative Demethylation of Dimethoxybenzenes 94 28.1.5.2.1.5 Method 5: Reaction of Maleoylcobalt Complexes with Alkynes 95 28.1.5.3 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen and One Bond to Nitrogen 96 28.1.5.3.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen and One Bond to Nitrogen 98 28.1.5.3.1.1 Method 1: Oxidation of Hydroquinones with Ammonium Cerium(IV) Nitrate 98 28.1.5.3.1.2 Method 2: Oxidation of Hydroquinones with Silver(l) Oxide 98 28.1.5.3.1.3 Method 3: Oxidation of Hydroquinones with Fungal Laccase 98 28.1.5.3.1.4 Method 4: Oxidative Demethylation of Dimethoxybenzenes 99 28.1.5.4 Benzo 1,4 quinones Substituted with Carbon with Three Bonds to Nitrogen 101 Table of Contents XVII 28.1.5.4.1 Synthesis of Benzol ,4 quinones Substituted with Carbon with Three Bonds to Nitrogen 101 28.1.5.4.1.1 Method 1: Oxidation of Hydroquinones with Silver Salts 101 28.1.5.4.1.2 Method 2: Oxidation of Hydroquinones with Manganese(IV) Oxide 102 28.1.6 Product Subclass 6: Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Heteroatoms M. Balci, M. Celik, and M. S. Giiltekin 28.1.6 Product Subclass 6: Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Heteroatoms 105 28.1.6.1 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Halogens 105 28.1.6.1.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Halogens 105 28.1.6.1.1.1 Method 1: Oxidative Demethylation of a 1,4 Dimethoxybenzene 105 28.1.6.2 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen — 106 28.1.6.2.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen 106 28.1.6.2.1.1 Method 1: Oxidation of 1,4 Hydroquinones with Silver(l) Oxide 106 28.1.6.2.1.2 Method 2: Oxidation of 1,4 Hydroquinones with Manganese(IV) Oxide 108 28.1.6.2.1.3 Method 3: Oxidation of a 1,4 Hydroquinone with 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone 109 28.1.6.2.1.4 Method 4: Oxidation of a 1,4 Hydroquinone Derivative in Aqueous Media 110 28.1.6.2.1.5 Method 5: Oxidative Demethylation of 1,4 Dimethoxybenzenes 110 28.1.6.2.2 Applications of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Oxygen in Organic Synthesis 111 28.1.6.3 Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Nitrogen •¦• 112 28.1.6.3.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with Two Bonds to Nitrogen 112 28.1.6.3.1.1 Method 1: Oxidation of a Diol with Manganese(IV) Oxide 112 28.1.7 Product Subclass 7: Benzo 1,4 quinones Substituted with Carbon with One Bond to a Heteroatom M. Balci, M. S. Gultekin, and M. Celik 28.1.7 Product Subclass 7: Benzo 1,4 quinones Substituted with Carbon with One Bond to a Heteroatom 115 28.1.7.1 Benzo 1,4 quinones Substituted with Carbon with One Bond to a Halogen •¦¦ 115 28.1.7.1.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with One Bond to a Halogen 115 28.1.7.1.1.1 Method 1: Demethylation of 1,4 Dimethoxybenzenes by Electrochemical Oxidation 115 XVIII Table of Contents 28.1.7.1.1.2 Method 2: Demethylation of Dimethoxybenzenes by Oxidation with Ammonium Cerium(IV) Nitrate 116 28.1.7.1.1.3 Method 3: Demethylation of Dimethoxybenzenes by Oxidation with Nitric Acid 116 28.1.7.1.1.4 Method 4: Allylic Bromination and Substitution 117 28.1.7.2 Benzo 1,4 quinones Substituted with Carbon with One Bond to Oxygen 119 28.1.7.2.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with One Bond to Oxygen 119 28.1.7.2.1.1 Method 1: (Diacetoxyiodo)benzene Oxidation 119 28.1.7.2.1.2 Method 2: Oxidation of Anilines 120 28.1.7.2.1.3 Method 3: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Nitric Acid 120 28.1.7.2.1.4 Method 4: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Ammonium Cerium(IV) Nitrate 121 28.1.7.2.1.5 Method 5: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Silver(l) Oxide 122 28.1.7.2.1.6 Method 6: Oxidation of Hydroquinones and 1,4 Dimethoxybenzenes with Iron(lll) Chloride 125 28.1.7.2.1.7 Methods 7: Additional Methods 126 28.1.7.3 Benzo 1,4 quinones Substituted with Carbon with One Bond to Sulfur 129 28.1.7.3.1 Synthesis of Benzo 1,4 quinones Substituted with Carbon with One Bond to Sulfur 129 28.1.8 Product Subclass 8: Alkynyl , Aryl , and Alkenyl Substituted Benzo 1,4 quinones M. Balci, M. S. Giiltekin, and M. Celik 28.1.8 Product Subclass 8: Alkynyl , Aryl , and Alkenyl Substituted Benzo 1,4 quinones 131 28.1.8.1 Alkynyl Substituted Benzo 1,4 quinones 131 28.1.8.1.1 Synthesis of Alkynyl Substituted Benzo 1,4 quinones 131 28.1.8.1.1.1 Method 1: Suzuki Cross Coupling of Benzo 1,4 quinones 131 28.1.8.1.1.2 Method 2: Oxidative Demethylation of 1,4 Dimethoxybenzenes 132 28.1.8.1.1.3 Method 3: Addition of Organolithium Compounds to Benzoquinone Derivatives 134 28.1.8.1.1.3.1 Variation 1: Addition to 2,5 Dialkoxybenzo 1,4 quinones 134 28.1.8.1.1.3.2 Variation 2: Addition to Dimethoxybenzo 1,2 quinones 135 28.1.8.2 Aryl Substituted Benzo 1,4 quinones 137 28.1.8.2.1 Synthesis of Aryl Substituted Benzo 1,4 quinones 137 28.1.8.2.1.1 Method 1: Coupling Reactions of Benzo 1,4 quinones 137 28.1.8.2.1.2 Method 2: Oxidative Demethylation and Coupling of a 1,4 Dimethoxybenzene 139 28.1.8.2.1.3 Method 3: Oxidation of 1,4 Hydroquinones Catalyzed by an Oxovanadium Complex 139 Table of Contents XIX 28.1.8.2.1.4 Method 4: Oxidation of Phenols and Derivatives Using Metals and Metal Oxides 140 28.1.8.2.1.5 Method 5: Oxidation of Phenols with Fremy's Salt 141 28.1.8.2.1.6 Method 6: Reaction of Fischer Carbene Complexes with Phenylacetylenes 142 28.1.8.2.1.7 Method 7: Reaction of Phenylacetylenes with a Tetracarbonyliron Species or with Carbon Monoxide 143 28.1.8.2.1.8 Methods 8: Additional Methods 144 28.1.8.3 Alkenyl Substituted Benzo 1,4 quinones 147 28.1.8.3.1 Synthesis of Alkenyl Substituted Benzo 1,4 quinones 147 28.1.8.3.1.1 Method 1: Direct Introduction of a Vinyl Group into Benzo 1,4 quinones 147 28.1.8.3.1.2 Method 2: Suzuki Cross Coupling of Benzo 1,4 quinones 147 28.1.8.3.1.3 Method 3: Oxidation of 1,4 Hydroquinones with Silver(l) Oxide 148 28.1.8.3.1.4 Method 4: Oxidation of a 1,4 Hydroquinone with 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone 149 28.1.8.3.1.5 Method 5: Oxidative Demethylation of 1,4 Dimethoxybenzenes with Ammonium Cerium(IV) Nitrate 150 28.1.8.3.1.6 Method 6: Electrochemical Oxidation of 1,4 Dimethoxybenzenes 150 28.1.8.3.1.7 Method 7: Thermal Ring Expansion of Cyclobutenedione Derivatives •¦• 151 28.1.8.3.1.8 Methods 8: Additional Methods 152 28.1.9 Product Subclass 9: Alkyl Substituted Benzo 1,4 quinones M. Balci, M. S. CGItekin, and M. Celik 28.1.9 Product Subclass 9: Alkyl Substituted Benzo 1,4 quinones 157 28.1.9.1 Monoalkylbenzo 1,4 quinones 157 28.1.9.1.1 Synthesis of Monoalkylbenzo 1,4 quinones 157 28.1.9.1.1.1 Method 1: Coupling Reactions of Benzo 1,4 quinones 157 28.1.9.1.1.2 Method 2: Oxidation of 1,4 Hydroquinones with an Organoselenium Reagent 158 28.1.9.1.1.3 Method 3: Oxidation of 1,4 Hydroquinones with Ammonium Cerium(IV) Nitrate 159 28.1.9.1.1.4 Method 4: Oxidation of Phenols and Derivatives 160 28.1.9.2 2,3 Dialkylbenzo 1,4 quinones 161 28.1.9.2.1 Synthesis of 2,3 Dialkylbenzo 1,4 quinones 161 28.1.9.2.1.1 Method 1: Oxidation of a 1,4 Hydroquinone with Silver(l) Oxide 161 28.1.9.2.1.2 Method 2: Oxidation of N Arylsulfonamides 161 28.1.9.2.1.3 Method 3: Reaction of Fischer Carbene Complexes with Alkynes 162 28.1.9.2.1.4 Methods 4: Additional Methods 162 28.1.9.3 2,5 Dialkylbenzo 1,4 quinones 165 28.1.9.3.1 Synthesis of 2,5 Dialkylbenzo 1,4 quinones 165 28.1.9.3.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones Using Methyltrioxorhenium(VII) 165 XX Table of Contents 28.1.9.3.1.2 Method 2: Oxidation of 1,4 Hydroquinones with Polymer Supported (Diacetoxyiodo)benzene 166 28.1.9.3.1.3 Method 3: Oxidation of 1,4 Hydroquinones and Derivatives with Ammonium Cerium(IV) Nitrate or Pyridinium Chlorochromate 166 28.1.9.3.1.4 Methods 4: Additional Methods 168 28.1.9.4 2,6 Dialkylbenzo 1,4 quinones 170 28.1.9.4.1 Synthesis of 2,6 Dialkylbenzo 1,4 quinones 170 28.1.9.4.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones 170 28.1.9.4.1.2 Method 2: Reaction of Acetylenes with a Carbonyliron Species 172 28.1.9.5 2,3,5 Trialkylbenzo 1,4 quinones 173 28.1.9.5.1 Synthesis of 2,3,5 Trialkylbenzo 1,4 quinones 173 28.1.9.5.1.1 Method 1: Oxidation of Phenols and 1,4 Hydroquinones 173 28.1.9.5.1.2 Methods 2: Additional Methods 174 28.1.9.6 2,3,5,6 Tetraalkylbenzo 1,4 quinones 175 28.1.9.6.1 Synthesis of 2,3,5,6 Tetraalkylbenzo 1,4 quinones 175 28.1.9.6.1.1 Method 1: Oxidation of 1,4 Hydroquinones and Derivatives 175 28.2 Product Class 2: Benzo 1,2 quinones V. Nair and K. V. Radhakrishnan 28.2 Product Class 2: Benzo 1,2 quinones 181 28.2.1 Synthesis of Product Class 2 182 28.2.11 Method 1: Oxidation of Catechols Using Silver(l) Salts 182 28.2.1.2 Method 2: Oxidation of Catechols Using Cerium(IV) Reagents 183 28.2.1.3 Method 3: Oxidation of Catechols Using Periodate Salts 184 28.2.14 Method 4: Oxidation of Catechols Using N Chlorosuccinimide 184 28.2.1.5 Method 5: Oxidation of Catechols Using Other Reagents 185 28.2.1.6 Method 6: Oxidation of Phenols Using Benzeneseleninic Anhydride 185 28J.U Method 7: Oxidation of Phenols Using Fremy's Salt 186 28.2.1.8 Method 8: Oxidation of Phenols Using Other Reagents 187 28.2.2 Applications of Product Class 2 in Organic Synthesis 187 28.2.2.1 Method 1: Addition of Nucleophiles 187 28.2.2.2 Method 2: Diels Alder and Related Reactions 195 28.2.2.2.1 Variation 1: Benzo 1,2 quinones as Carbodienes and Heterodienes 195 28.2.2.2.2 Variation 2: Benzo 1,2 quinones as Dienophiles 196 28.2.2.2.3 Variation 3: Benzo 1,2 quinones as Heterodienophiles 198 28.2.2 3 Method 3: Dipolar Cydoadditions 198 28J.2.3.1 Variation 1: Nitrile Oxide Addition 198 28.2.2.3.2 Variation 2: Diazomethane Addition 200 28J.2.3.3 Variation 3: Acyclic Carbonyl Ylide Addition 200 28.2.2.3.4 Variation 4: Cyclic Carbonyl Ylide Addition 201 28.2.2.3.5 Variation 5: Addition of Mesoionic Compounds 202 28.2.2.3.6 Variation 6: Addition of Phosphorus Ylides 204 Table of Contents XXI 28.2.2 4 Method 4: Multicomponent Reactions 205 28.2.2.4.1 Variation 1: Addition of Zwitterions Generated from Isocyanides and Dimethyl Acetylenedicarboxylate 205 28.2.2.4.2 Variation 2: Addition of Zwitterions Generated from Dialkoxycarbenes and Dimethyl Acetylenedicarboxylate 207 28.2.2.5 Methods 5: Additional Methods 208 283 Product Class 3: Naphtho 1,4 quinones E. A. Couladouros and A. T. Strongilos 283 Product Class 3: Naphtho 1,4 quinones 217 283.1 Synthesis of Product Class 3 220 283.1.1 Synthesis by Ring Closure Reactions 220 283.1.1.1 Method 1: Reaction of Fischer Type Carbene Complexes with Alkynes 220 283.1.1.2 Method 2: Synthesis from Cyclobutenediones 225 283.1.1.2.1 Variation 1: Reaction of Phthaloyl Complexes with Functionalized Alkynes 229 283.1.1.3 Method 3: Annulation Reactions of Phthalide Anions with Michael Acceptors 232 283.1.1.4 Method 4: [4+ 2] Cycloaddition Reactions 234 283.1.1.4.1 Variation 1: Reaction of Benzo 1,4 quinones with Heterosubstituted Dienes 239 283.1.1.4.2 Variation 2: Reaction of Benzo 1,4 quinones with Vinylarenes and Vinylhetarenes 241 283.1.1.4.3 Variation 3: Reaction of Benzo 1,4 quinones with Dienes of Fixed s cis Conformation 242 283.1.1.4.4 Variation 4: Quinones as Dienes 245 283.1.1.5 Method 5: Condensation of Benzaldehydes with Succinic Acid Derivatives 246 283.1.1.6 Method 6: Friedel Crafts Condensation of Hydroquinone Derivatives with Maleic Anhydrides 248 283.1.1.7 Method 7: Annulation of ortho Substituted Tertiary Benzamides 250 283.1.2 Synthesis by Oxidative Transformation 251 283.1.2.1 Method 1: Oxidation of Naphthalenes 252 283.1.2.1.1 Variation 1: Oxidation of Naphthalene Derivatives Bearing Oxidation Directing Groups 255 283.1.2.2 Method 2: Oxidation of Naphthols 255 283.1.2.3 Method 3: Oxidation of Hydroquinone Derivatives 261 283.1.2.3.1 Variation 1: Oxidation of Diprotected Hydroquinone Derivatives 261 283.1.2.3.2 Variation 2: Oxidation of Monoprotected Hydroquinone Derivatives 263 283.1.2.3.3 Variation 3: Oxidation of Hydroquinones 264 283.1.2.4 Method 4: Oxidation of Naphthols Bearing Substituents Other Than Oxygen at the 4 Position 265 283.1.2.5 Method 5: Aromatization and Benzylic Oxidation of Fused Carbocycles 267 283.1.3 Substitution of Hydrogen 267 283.1.3.1 Method 1: Using Nucleophilic Carbon Reagents 268 XXII Table of Contents 283.1.3.2 Method 2: Using Electrophilic Carbon Reagents 271 28.3.13 3 Method 3: Using Carbon Free Radicals 273 283.1.3.4 Method 4: Addition of Halides 277 283.1.3.5 Method 5: Varvoglis' lodonium Ylides 279 283.1.3.6 Method 6: Using Oxygen Nucleophiles 280 283.1.3.7 Method 7: TheThiele Winter Acetoxylation Reaction 282 283.1.3.8 Method 8: Using Sulfur Nucleophiles 283 283.1.3.9 Method 9: Addition of Amines, Azides, and Ammonia 286 283.1.4 Substitution of Heteroatoms 289 283.1.4.1 Method 1: Substitution of Halogen by Another Halogen 289 283.1.4.2 Method 2: Substitution of Halogen by Oxygen 289 283.1.4.3 Method 3: Substitution of Halogen by Sulfur 291 283.1.4.4 Method 4: Substitution of Halogen by Nitrogen 292 283.1.4.5 Method5: Substitution of Halogen by Carbon 294 283.1.4.5.1 Variation 1: Palladium Mediated Coupling of Halogenated Naphtho 1,4 quinones 295 283.1.4.6 Method 6: Substitution of Oxygen by Halogen, Nitrogen, or Carbon — 297 28.4 Product Class 4: Naphtho 1,2 , Naphtho 1,5 , Naphtho 1,7 , Naphtho 2,3 , and Naphtho 2,6 quinones C. C. Liao and R. K. Peddinti 28.4 Product Class 4: Naphtho 1,2 , Naphtho 1,5 , Naphtho 1,7 , Naphtho 2,3 , and Naphtho 2,6 quinones 323 28.4.1 Product Subclass 1: Naphtho 1,2 quinones 323 28.4.1.1 Synthesis of Product Subclass 1 325 28.4.1.1.1 Method 1: Reaction of Fischer Type Carbene Complexes with tert Butyl Isocyanide 325 28.4.1.1.2 Method 2: [4+ 2] Cycloaddition Reactions 325 28.4.1.1.2.1 Variation 1: Reaction of Benzoquinones with 2,3 Dimethylbuta 1,3 diene 325 28.4.1.1.2.2 Variation 2: Reaction of Dihalocatechols with 1 (Trimethylsiloxy)buta 1,3 diene 326 28.4.1.1.3 Method 3: Dieckmann Ring Formation with Subsequent Acyloin Cleavage 327 28.4.1.1.4 Method 4: Oxidation of a Tetralones 327 28.4.1.1.5 Method 5: Oxidation of Naphthalenes 328 28.4.1.1.6 Method 6: Oxidation of 1 Naphthols 329 28.4.1.1.6.1 Variation 1: Oxidation of 1 Naphthols with Fremy's Salt 329 28.4.1.1.6.2 Variation 2: Oxidation of 1 Naphthols with Benzeneseleninic Anhydride 332 28.4.1.1.6.3 Variation 3: Oxidation of 1 Naphthols with Cobalt Salen Complex/Oxygen 332 28.4.1.1.6.4 Variation 4: Synthesis of Emmotin H Using lodylbenzene 333 28.4.1.1.6.5 Variations: Oxidation of a 1 Naphthol Derivative with Sodium Periodate 333 28jI.i.i.6.6 Variation 6: Oxidation of Halo 1 naphthols with Lead(IV) Acetate 334 28^4.1.1.6.7 Variation 7: Transition Metal Catalyzed Oxidations of 1 Naphthols 334 28A1.1.7 Method 7: Oxidation of 2 Naphthols 336 Table of Contents XXIII 28.4.1.1.7.1 Variation 1: Oxidation of 2 Naphthol 336 28.4.1.1.7.2 Variation 2: Oxidation of 2 Naphthols with Fremy's Salt 336 28.4.1.1.7.3 Variation 3: Synthesis of o Hibiscanone with Benzeneseleninic Anhydride 337 28.4.1.1.7.4 Variation 4: Oxidation of 2 Naphthols with Copper Chloride/Oxygen 337 28.4.1.1.7.5 Variation 5: Oxidation of 2 Naphthols with 3 Chloroperoxybenzoic Acid 338 28.4.1.1.7.6 Variation 6: Transition Metal Catalyzed Oxidations of 2 Naphthols 339 28.4.1.1.7.7 Variation 7: Oxidation of 1 Amino 2 naphthol by Polymer Supported Hypochlorite Ion 339 28.4.1.1.8 Method 8: Oxidation of Naphthalene 1,2 diols 339 28.4.1.1.8.1 Variation 1: Oxidation of Naphthalene 1,2 diol 340 28.4.1.1.8.2 Variation 2: Synthesis from Naphthalene 1,2 diol Disilyl Ether 340 28.4.1.1.8.3 Variation 3: Aerial Oxidation of Naphthalene 1,2 diols 341 28.4.1.1.8.4 Variation 4: Synthesis of Saprorthoquinone via Silver(l) Oxide Oxidation 342 28.4.1.1.8.5 Variation 5: Oxidation of Naphthalene 1,2 diol with Oxygen and Bis(propane 1,3 diamine)copper(ll) Chloride 342 28.4.1.1.9 Method 9: Oxidation of a 1 Methoxynaphthalen 2 amine Derivative — 342 28.4.1.1.10 Method 10: Rearrangement of Naphtho 1,4 quinone Adducts 343 28.4.1.1.11 Method 11: Substitution of Hydrogen 343 28.4.1.1.11.1 Variation 1: Reaction of Naphtho 1,2 quinone with Pyrroles 343 28.4.1.1.11.2 Variation 2: Reaction of Naphtho 1,2 quinone with Vinylogous Michael Donors 344 28.4.1.1.11.3 Variation 3: Lewis Acid Mediated Reactions of Naphtho 1,2 quinones — 344 28.4.1.1.H.4 Variation 4: Palladium(ll) Catalyzed Oxidative Coupling of Naphtho 1,2 quinone and Arenes 345 28.4.1.1.11.5 Variation 5: Photochemical Reactions of Naphtho 1,2 quinones 345 28.4.1.1.11.6 Variation 6: Reactions of Naphtho 1,2 quinones with Amines 348 28.4.1.1.11.7 Variation 7: Reactions of 4 Aminonaphtho 1,2 quinone with Diazenes ¦•• 349 28.4.1.1.11.8 Variation 8: Metal Chloride Catalyzed Addition of Alcohols to Naphtho 1,2 quinones 350 28.4.1.1.11.9 Variation 9: Reactions of Naphtho 1,2 quinones with Thiols 351 28.4.1.1.12 Method 12: Substitution of Heteroatoms 351 28.4.1.1.12.1 Variation 1: Reactions of 4 Alkoxynaphtho 1,2 quinones with Amines ••• 351 28.4.1.1.12.2 Variation 2: Reactions of Sodium 4 Sulfonatonaphtho 1,2 quinone 352 28.4.1.1.13 Method 13: Alkylation of the Silver Salt of 2 Hydroxynaphtho 1,4 quinones 355 28.4.2 Product Subclass 2: Naphtho 1,5 quinones 356 28.4.2.1 Synthesis of Product Subclass 2 356 28.4.2.1.1 Method 1: Oxidation of a 2,3 Dihydronaphtho 1,4 quinone Imine 356 28.4.2.1.2 Method 2: Oxidation of Naphthalene 1,5 diols 356 28.4.2.1.2.1 Variation 1: Air Oxidation of a Naphthalene 1,5 diol 356 28.4.2.1.2.2 Variation 2: 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone Oxidation of 3,7 Di tert butylnaphthalene 1,5 diol357 28.4.2.1.3 Method 3: Substitution of Hydrogen by Halogen 357 28.4.2.1.3.1 Variation 1: Substitution of Hydrogen by Chlorine 357 28.4.2.1.3.2 Variation 2: Substitution of Hydrogen by Bromine 358 28.4.2.1.4 Method 4: Substitution of 4,8 Diaminonaphtho 1,5 quinone 358 XXIV Table of Contents 28.4.3 Product Subclass 3: Naphtho 1,7 quinones 358 28.4.3.1 Synthesis of Product Subclass 3 358 28.4.3.1.1 Method 1: 2,3 Dichloro 5,6 dicyanobenzo 1,4 quinone Oxidation of 3,6 Di tert butyl 8 methylnaphthalene 1,7 diol 358 28.4.4 Product Subclass 4: Naphtho 2,3 quinones 359 28.4.4.1 Synthesis of Product Subclass 4 359 28.4.4.1.1 Method 1: Generation and Trapping through Desilylation Debromination Induced by Fluoride Ion 359 28.4.4.1.2 Method 2: Oxidation of 1,4 Diarylnaphthalene 2,3 diols 360 28.4.5 Product Subclass 5: Naphtho 2,6 quinones 362 28.4.5.1 Synthesis of Product Subclass 5 362 28.4.5.1.1 Method 1: Photooxygenation of Naphthalen 2 amine 362 28.4.5.1.2 Method 2: Oxidation of a Naphthalene 2,6 diol with Lead(IV) Oxide • • • • 362 283 Product Class 5: Anthra 9,10 quinones, Anthra 1,2 quinones, Anthra 1,4 quinones, Anthra 2,9 quinones, and Their Higher Fused Analogues K. Krohn and N. Boker 28.5 Product Class 5: Anthra 9,10 quinones, Anthra 1,2 quinones, Anthra 1.4 quinones, Anthra 2,9 quinones, and Their Higher Fused Analogues 367 28.5.1 Product Subclass 1: Anthra 9,10 quinones 367 28.5.1.1 Synthesis of Product Subclass 1 369 28.5.1.1.1 Friedel Crafts Reactions 369 28.5.1.1.1.1 Method 1: One Pot Procedures Using Fused Salts (N Alkylpyridinium Halides) with Aluminum Trichloride as the Catalyst 371 28.5.1.1.1.2 Method 2: One Pot Procedures Using Molten Aluminum Trichloride Potassium Chloride Sodium Chloride or Aluminum Trichloride Sodium Chloride as the Catalysts 372 28.5.1.1.1.3 Method 3: One Pot Procedures Using Croup 4 or Croup 5 Metal Oxides as the Catalysts 373 28.5.1.1.1.4 Method 4: One Pot Procedures Using Phthaloyl Dichlorides as the Electrophiles 373 28.5.1.1.1.5 Method 5: Stepwise Procedures with Benzoylbenzoic Acids as the Intermediates 374 283.1.1.1.5.1 Variation 1: Benzoylbenzoic Acids by Friedel Crafts Reaction 375 28.5.1.1.1.5.2 Variation 2: Benzoylbenzoic Acids by Addition of Crignard Reagents to Phthalic Anhydrides 375 28.5.1.1.1.6 Method 6: Stepwise Procedures Involving Direct Cyclization of Benzoylbenzoic Acids 376 283.1.1.1.7 Method 7: Stepwise Procedures Involving Sequential Cyclization of Benzylbenzoic Acids and Oxidation 378 Table of Contents XXV 28.5.1.1.1.8 Method 8: Stepwise Procedures Involving Benzylbenzoic Acids Prepared by Displacement of a Methoxy Group in Aryldihydrooxazoles 380 28.5.1.1.1.9 Method 9: Stepwise Procedures Involving Friedel Crafts Type Alkylation of 3 Bromophthalides with Benzenes To Form 3 Arylphthalides 381 28.5.1.1.2 Diels Alder Reactions 382 28.5.1.1.2.1 Method 1: Reaction of Open Chain Dienes with Naphtho 1,4 quinones Followed by Elimination or Oxidation of Allylic Hydroxy Croups 383 28.5.1.1.2.2 Method 2: Reaction of Open Chain Dienes with Naphtho 1,4 quinones Followed by Two p Eliminations 388 28.5.1.1.2.2.1 Variation 1: Reaction of 1,3 Siloxy 1,3 dienes with Halonaphtho 1,4 quinones 388 28.5.1.1.2.2.2 Variation 2: Reaction of 1,3 Siloxy 1,3 dienes with Dichloronaphtho 1,4 quinones 390 28.5.1.1.2.2.3 Variation 3: Reaction of Vinylketene Acetals with 2 or3 Halonaphtho 1,4 quinones 391 28.5.1.1.2.2.4 Variation 4: Diels Alder Reactions of Sulfinylnaphtho 1,4 quinones 395 28.5.1.1.2.3 Method 3: Reaction of Cyclic Dienes with Naphtho 1,4 quinones, Followed by a Retro Diene Reaction 395 28.5.1.1.2.4 Method 4: Reaction of Cyclic Dienes with Naphtho 1,4 quinones Followed by Hydroxymethylation of 1,4 Ethanoanthra 9,10 quinones 399 28.5.1.1.2.5 Method 5: Reaction of Naphtho 1,4 quinones with Ketene Acetals 400 28.5.1.1.2.6 Method 6: Coupling of Naphtho 1,4 quinones with Cyclobutenones — 401 28.5.1.1.2.7 Method 7: Thermolytic Rearrangement of Arylcyclobutenones 401 28.5.1.1.2.8 Method 8: Electrocyclization of 2,3 Divinylnaphtho 1,4 quinones 402 28.5.1.1.2.9 Method 9: Electrocyclization of 2,3 Divinylnaphtho 1,4 quinones to 1,4 Diacylanthra 9,10 quinones 403 28.5.1.1.3 Ring Closing Metathesis 404 28.5.1.1.3.1 Method 1: Cyclization of 2,3 Diallylnaphtho 1,4 quinones 404 28.5.1.1.4 [2 + 2 + 2] Cycloaddition Reactions 406 28.5.1.1.4.1 Method 1: Rhodium Catalyzed Cycloaddition of 1,2 Dipropynoylbenzenes with Alkynes 406 28.5.1.1.5 Anionic Condensation Reactions 407 28.5.1.1.5.1 Method 1: Phthalide Annulation with Cyclohex 2 enones 407 28.5.1.1.5.2 Method 2: Phthalide Annulation with Cyclohexadienones 408 28.5.1.1.5.2.1 Variation 1: With Cyclohexa 2,5 dienones 409 28.5.1.1.5.2.2 Variation 2: With Cyclohexa 2,4 dienones 410 28.5.1.1.5.3 Method 3: Phthalide Annulation with Arynes 410 28.5.1.1.6 Cyclization by Nucleophilic Aromatic Substitution/Addition 411 28.5.1.1.6.1 Method 1: Cyclization of 2 (Cyanomethyl)benzophenones (The Hassall Reaction) 411 28J.1.1.6.2 Method 2: Addition of 2 (Cyanomethyl)benzoates to Arynes 412 28.5.1.1.6.3 Method 3: Cyclization of (Nitromethyl)benzophenones 413 XXVI Table of Contents 283.1.1.6.4 Method 4: Cyclization of Monoalkylnaphtho 1,4 quinones 414 28.5.1.1.6.5 Method 5: Cyclization of 2,3 Disubstituted Naphtho 1,4 quinones by Aldol Condensation 414 28.5.1.1.6.5.1 Variation 1: Michael Addition of 2 Acetylnaphtho 1,4 quinones 415 28.5.1.1.6.5.2 Variation 2: Base Induced Condensation of 2 Acylnaphtho 1,4 quinones 415 28.5.1.1.6.6 Method 6: Cyclization of 2,3 Dialkylnaphtho 1,4 quinones by Reaction of Enamines with 2 Acetylnaphtho 1,4 quinones ••• 416 28.5.1.1.6.7 Method 7: Cyclization of 2,3 Dialkylnaphtho 1,4 quinones by Iterative Addition of 1,3 Dicarbonyl Dianions 417 28.5.1.1.6.7.1 Variation 1: Addition of 1,3 Dicarbonyl Dianions to Homophthalic Diesters 417 28.5.1.1.6.7.2 Variation 2: Addition of 1,3 Dicarbonyl Dianions to Homophthalic Monoesters 418 28.5.1.1.7 Oxidation of Anthracenes to Anthra 9,10 quinones 419 28.5.1.1.7.1 Method 1: Catalytic Oxidation of Anthracene with Dioxygen in the Presence of Nitrogen Dioxide 420 28.5.1.1.7.2 Method 2: Transition Metal Catalyzed Liquid or Vapor Phase Aerial Oxidation of Anthracene 421 283.1.1.7.3 Method 3: Anodic Oxidation of Anthracene 421 283.1.1.7.4 Method 4: Catalytic Oxidation of Anthracene with Other Sources of Oxygen 422 283.1.1.7.5 Method 5: Stoichiometric Oxidations of Anthracene 423 283.1.1.8 Oxidative Cyclization Reactions of 2 Benzyl Substituted Diphenylmethanes 424 28.5.1.1.8.1 Methodi: Oxidation of 1 Benzyl 2 methylbenzene 424 283.1.1.9 Oxidation of Dihydroanthra 9,10 quinones or Anthracen 9(10H) ones to Anthra 9,10 quinones 424 283.1.1.9.1 Methodi: Aerial Oxidation of Anthracen 9(10H) one or 9,10 Dihydroanthracenes 424 283.1.1.9.2 Method 2: Oxidation of Anthracen 9(10H) ones, 10 Hydroxyanthracen 9(10H) ones, or Hydroquinone Methyl Ethers by Ammonium Cerium(IV) Nitrate 425 283.1.1.10 Oxidation of meso Benza nth rones and Aromatic Carbocycles 425 283.1.1.11 Alkylation Reactions 425 283.1.1.11.1 Methodi: Addition of Nitroalkanes to Hydroxyanthra 9,10 quinones ••• 426 283.1.1.11.2 Method 2: Addition of Malonate to Hydroxyanthra 9,10 quinones 426 283.1.1.11.3 Method 3: Alkylation of 1,4 Dihydroxyanthra 9,10 quinone via Anthracene 1,4,9,10 tetrone and a 1,5 Alkyl Shift 427 283.1.1.11.4 Method 4: Alkylation with Intermediate Reduction 427 283.1.1.11.4.1 Variation 1: Alkylation under Strongly Basic Conditions (Marschalk Conditions) 427 283.1.1.11.4.2 Variation 2: Alkylation with Piperidine Acetate as the Catalyst (Lewis Conditions) 429 283.1.1.11.4.3 Variation 3: Alkylation with Pyrrolidine as the Catalyst (Broadbent Conditions) 430 283.1.1.11.4.4 Variation 4: Hydroxyalkylation of peri Hydroxyanthra 9,10 quinones (Modified Marschalk Reaction) 431 Table of Contents XXVII 28.5.1.U1.4.5 Variation 5: 1,5 Oiazabicyclo[5.4.0]undec 7 ene or 1,5 Diazabicylo[4.3.0] non 5 ene in Tetrahydrofuran in Marschalk Reactions 432 28.5.1.1.11.4.6 Variation 6: Successive Marschalk Reactions in Syntheses of 2,3 Dialkylanthra 9,10 quinones 434 28.5.1.1.11.4.7 Variation 7: Addition of 1 Hydroxyanthra 9,10 quinones and Their Tautomers to Michael Acceptors 434 28.5.1.1.11.4.8 Variation 8: Alkylation of 1 Aminoanthra 9,10 quinones 435 28.5.1.1.11.4.9 Variation 9: Alkylation of 1 Hydroxyanthra 9,10 quinones 435 28.5.1.1.11.5 Method 5: Alkylation of Anthra 9,10 quinones by the Reductive Claisen Rearrangement 436 28.5.1.1.11.6 Method 6: Alkylation by a Combination of the Marschalk Reaction and the Reductive Claisen Rearrangement 437 28.5.1.1.11.7 Method 7: Alkylation via Diazonium Ions 438 28.5.1.1.12 Arylation Reactions 439 28.5.1.1.13 Alkenylation Reactions 439 28.5.1.1.14 Alkynylation Reactions 439 28.5.1.1.14.1 Methodi: Isomerization of Allylanthra 9,10 quinones 439 28.5.1.1.15 Halogenation Reactions 440 28.5.1.1.15.1 Methodi: Fluorination 440 28.5.1.1.15.2 Methodi: Chlorination 440 28.5.1.1.15.3 Method 3: Bromination 441 28.5.1.1.15.4 Method 4: lodination 443 28.5.1.1.16 Sulfonation Reactions 443 28.5.1.1.17 Amination Reactions 444 28.5.1.1.18 Hydroxylation Reactions 445 28.5.1.1.19 Nitration Reactions 445 28.5.1.1.20 Synthesis by Substitution 447 28.5.1.1.20.1 Methodi: Substitution of Fluoride 447 28.5.1.1.20.2 Method 2: Substitution of Chloride 448 28.5.1.1.20.3 Method 3: Substitution of Bromide or Iodide 450 28.5.1.1.20.3.1 Variation 1: Substitution of Bromide and Iodide by Heteroatoms 450 283.1.1.20.3.2 Variation 2: Substitution of Bromide by Aryl Croups (The Heck Reaction) 450 28.5.1.1.20.3.3 Variation 3: Substitution of Bromide and Iodide by Acetylene Nucleophiles 451 28.5.1.1.20.3.4 Variation 4: Substitution of Iodide with Tin Nucleophiles 453 28.5.1.1.20.4 Method 4: Substitution of Nitro Croups 453 28.5.1.1.20.5 Method 5: Substitution of Trifluoromethanesulfonates 454 28.5.2 Product Subclass 2: Anthra 1,2 quinones 455 28.5.2.1 Synthesis of Product Subclass 2 455 28.5.2.1.1 Oxidation Reactions 455 28.5.2.1.1.1 Methodi: Oxidation of 1,2 Dihydroxyanthracenes 455 28.5.2.1.1.2 Method 2: ortho Specific Oxygenation of 1 Anthrols 456 XXVIII Table of Contents 28.5.3 Product Subclass 3: Anthra 1,4 quinones 457 28.5.3.1 Synthesis of Product Subclass 3 457 28.5.3.1.1 Fixation of the 1,4 Dicarbonyl Tautomer of 1,4 Dihydroxyanthra 9,10 quinone 457 28.5.3.1.1.1 Method!: Chlorination of 1,4 Dihydroxyanthra 9,10 quinone 457 28.5.3.1.1.2 Method 2: Transesterification of N,O,O Triacylated 1,4 Dihydroxy 10 iminoanthracen 9(10H) ones 458 28.5.3.1.2 Diels Alder Reactions 458 28.5.3.1.2.1 Method 1: Addition of Quinodimethanes to Benzoquinones 458 28.5.3.1.2.2 Method 2: Strong Base Mediated Addition of Homophthalic Anhydrides to Benzoquinones 459 28.5.3.1.2.3 Method 3: Tandem Claisen Diels Alder Reactions 460 28.5.3.1.2.4 Method 4: Phthalide Annulation 461 28.5.4 Product Subclass 4: Anthra 2,9 quinones 461 28.5.5 Product Subclass 5: Anthraquinones Fused with Other Carbon Rings 462 283.5.1 Synthesis of Product Subclass 5 462 28.5.5.1.1 Synthesis of Anthraquinones Fused with Four Membered Rings 462 28.5.5.1.1.1 Method 1: Double Aldol Condensation 462 28.5.5.1.2 Synthesis of Anthraquinones Fused with Five Membered Rings 463 28.5.5.1.2.1 Method 1: Friedel Crafts Reaction of Phthalic Anhydride with Indanes 463 28.5.5.1.2.2 Method 2: Diels Alder Reactions of Naphtho 1,4 quinone with 1 Vinylcyclopentenes 463 28.5.5.1.2.3 Method 3: Cyclization of Monoalkylanthra 9,10 quinones 463 28.5.5.1.2.4 Method 4: Cyclization of 2,3 Dialkylanthra 9,10 quinones 464 28.5.5.1.3 Synthesis of Anthraquinones Fused with Six Membered Rings: Tetracene 5,12 diones 465 28.5.5.1.3.1 Method 1: One Pot Friedel Crafts Condensation 466 28.5.5.1.3.1.1 Variation 1: Double Friedel Crafts Condensation with Phthalic Anhydride 466 28.5.5.1.3.1.2 Variation 2: Successive Fries Shift and Friedel Crafts Reaction 466 28.5.5.1.3.2 Method 2: Multistep Friedel Crafts Condensation 467 28.5.5.1.3.2.1 Variation 1: Friedel Crafts Reaction of Benzylbenzoic Acids 467 28J.5.1.3.2.2 Variation 2: Friedel Crafts Reaction of a Lactone 468 28.5.5.1.3.2.3 Variation 3: Friedel Crafts Reaction of Benzoylbenzoic Acids 468 28.5.5.1.3.3 Method 3: Tetracene 5,12 diones by Diels Alder Reactions: Trapping of o Quinodimethanes with Dienes 469 28.5.5.1.3.3.1 Variation 1: Intermolecular Trapping of o Quinodimethanes 470 28.5.5.1.3.3.2 Variation 2: Intramolecular Trapping of o Quinodimethanes 471 28.5.5.1.3.4 Method 4: Diels Alder Reactions of Anthra 1,4 quinones and Derivatives as the Dienophiles 471 28J.5.1.3.4.1 Variation 1: Anthra 1,4 quinones as the Dienophiles 471 28.5.5.1.3.4.2 Variation 2: Anthracenetetrones as the Dienophiles 472 28.5.5.1.3.4.3 Variation 3: Anthradiquinone Epoxides as the Dienophiles 473 28J.5.1.3.4.4 Variation 4: 1,4 Dihydroxyanthra 9,10 quinone and Its 9 lmine as Dienophiles 474 28.5.5.1.3.4.5 Variation 5: Partially Hydrogenated or Bridged Anthra 9,10 quinones — 474 Table of Contents XXIX 28.5.5.1.3.5 Method 5: Diels Alder Reactions with Benzocyclobutenes as the Diene Precursors 475 28.5.5.1.3.6 Method 6: Diels Alder Reactions of Exocyclic Dienes and Exocyclic Vinylketene Acetals 476 28.5.5.1.3.7 Method 7: Strong Base Induced Cycloaddition of Homophthalic Anhydrides to Naphthoquinones 477 28.5.5.1.3.8 Method 8: Intramolecular Diels Alder Reactions 478 28.5.5.1.3.9 Method 9: Anionic Cyclization of Monoalkylanthra 9,10 quinones 479 28.5.5.1.3.9.1 Variation 1: Cyclization of Nitronatoanthra 9,10 quinones 479 28.5.5.1.3.9.2 Variation 2: Cyclization of 4 Hydroxy 2 (4 oxobutyl)anthra 9,10 quinone 480 28.5.5.1.3.10 Method 10: Anionic Cyclization of Dialkylanthra 9,10 quinones 481 28.5.5.1.3.10.1 Variation 1: Biomimetic Oxo Ester Cyclization 481 28.5.5.1.3.10.2 Variation 2: Lewis Acid Mediated Cyclization of ort/io Allyl Substituted Dioxolanyl Anthraquinones and Formylanthraquinones 482 28.5.5.1.3.10.3 Variation 3: Base Catalyzed Cyclization of a Nonsymmetrically Substituted 2,3 Diallylanthra 9,10 quinone 482 28.5.5.1.3.11 Method 11: 1,4 Dipolar Additions to Enones and Arynes 483 28.5.5.1.4 Synthesis of Anthraquinones Fused with Six Membered Rings: Tetraphene 7,12 diones 484 28.5.5.1.4.1 Method 1: Friedel Crafts Reactions 484 28.5.5.1.4.2 Method 2: Diels Alder Reactions 484 28.5.5.1.4.3 Method 3: Anionic Cyclizations 485 28.5.5.1.4.3.1 Variation 1: Cyclization of Monoalkylanthra 9,10 quinones 485 28.5.5.1.4.3.2 Variation 2: Cyclization of Dialkylanthra 9,10 quinones 486 28.5.5.1.4.4 Method4: [2 + 2 + 2] Cycloaddition 486 28.5.5.1.4.5 Method5: Rearrangement of Spiroanthracenediones 487 28.6 Product Class 6: Phenanthrene 9,10 diones, Stilbenequinones, Diphenoquinones, and Related Ring Assemblies A. M. Echavarren and S. Porcel 28.6 Product Class 6: Phenanthrene 9,10 diones, Stilbenequinones, Oiphenoquinones, and Related Ring Assemblies 507 28.6.1 Product Subclass 1: Phenanthrene 9,10 diones 507 28.6.1.1 Synthesis of Product Subclass 1 508 28.6.1.1.1 Method 1: Direct Oxidation of Polycyclic Arenes 508 28.6.1.1.1.1 Variation 1: Oxidation with Stoichiometric Oxidizing Reagents 508 28.6.1.1.1.2 Variation 2: Oxidation with Catalytic Oxidizing Reagents 511 28.6.1.1.2 Method 2: Ring Closure Reactions 512 28.6.1.1.2.1 Variation 1: Oxidative Biaryl Coupling of a Dicarbonyl Compounds 512 28.6.1.1.2.2 Variation 2: Photochemical Cyclization 513 28.6.1.1.2.3 Variation 3: Reductive Coupling of Carbonyls 516 28.6.1.2 Applications of Product Subclass 1 in Organic Synthesis 518 28.6.1.2.1 Method 1: Synthesis of Functionalized Fused Furans 518 XXX Table of Contents 28.6.1.2.2 Method 2: Catalyzed Epoxidation in the Presence of Phenanthrene 9,10 dione 519 28.6.1.2.3 Method 3: Synthesis of Heterocycles 519 28.6.1.2.4 Method 4: Synthesis of Biphenyl 2,2' dicarboxylic Acids 521 28.6.1.2.5 Method 5: Protection of 1,2 Diols 521 28.6.1.2.6 Method 6: Synthesis of Polycyclic Arenes via Bis Wittig Reactions 522 28.6.2 Product Subclass 2: Heterocyclic Analogues of Phenanthrene 9,10 diones 523 28.6.2.1 Synthesis of Product Subclass 2 524 28.6.2.1.1 Method 1: Oxidation of Hetarenes 524 28.6.2.1.1.1 Variation 1: Direct Oxidation of Hetarenes 524 28.6.2.1.1.2 Variation 2: Chlorination of Hetarenes 527 28.6.2.1.1.3 Variation 3: Oxidation of Hydroxy and/or Alkoxy Substituted Hetarenes with Strong Oxidants 528 28.6.2.1.1.4 Variation 4: Oxidation of Hydroxy and/or Alkoxy Substituted Hetarenes with Mild Oxidants 531 28.6.2.1.1.5 Variation 5: Oxidation of Amino Substituted Hetarenes 535 28.6.2.1.2 Method 2: Ring Closure Reactions 537 28.6.2.1.2.1 Variation 1: N—C Bond Forming Reactions 537 28.6.2.1.2.2 Variation 2: C—C Bond Forming Reactions 538 28.6.2 2 Applications of Product Subclass 2 in Organic Synthesis 539 28.6.2.2.1 Method 1: Oxidation of Functional Croups 539 28.6.3 Product Subclass 3: Stilbenequinones 541 28.6.3.1 Synthesis of Product Subclass 3 542 28.6.3.1.1 Method 1: Oxidation of Dihydroxystilbenes 543 28.6.3.1.2 Method 2: Oxidative Dimerization of Aromatic Compounds 544 28.6.3.1.2.1 Variation 1: Oxidation Dimerization of Phenols 544 28.6.3.1.2.2 Variation 2: Oxidative Dimerization of 2,4,6 Trimethylphenyl Chloroformate 547 28.6.3.2 Applications of Product Subclass 3 in Organic Synthesis 547 28.6.3.2.1 Method 1: Acid Catalyzed Rearrangement of Stilbenequinones 547 28.6.4 Product Subclass 4: Diphenoquinones 548 28.6.4.1 Synthesis of Product Subclass 4 550 28.6.4.1.1 Method 1: Oxidation of Biphenyldiols 550 28.6.4.1.2 Method 2: Oxidative Coupling of Phenols 551 28.6.4.1.2.1 Variation 1: Oxidative Coupling Using Stoichiometric Oxidants 551 28.6.4.1.2.2 Variation 2: Oxidative Coupling with Metal Catalysts 553 28.6.4.1.2.3 Variation 3: Enzymatic Oxidative Coupling 555 Table of Contents XXXI 28.7 Product Class 7: Hetarene Fused Quinones 28.7.1 Product Subclass 1: Nitrogen Containing Hetarene Quinones U. Pindur and T. Lemster 28.7.1 Product Subclass 1: Nitrogen Containing Hetarene Quinones 561 28.7.1.1 Synthesis of Product Subclass 1 561 28.7.1.1.1 Nitrogen Containing Hetarene p Quinones 561 28.7.1.1.1.1 Indolequinones, Carbazolequinones, and Higher Analogues 561 28.7.1.1.1.1.1 Method 1: Direct Oxidation of Hydroquinone Derivatives 562 28.7.1.1.1.1.2 Method 2: Ring Closure Reactions of Pyrroles 563 28.7.1.1.1.1.3 Method 3: Ring Closure Reactions of Substituted Benzoquinones 564 28.7.1.1.1.1.4 Method 4: Ring Expansion of Cyclobutenone Derivatives 566 28.7.1.1.1.2 Naphthindolizinequinones 567 28.7.1.1.1.2.1 Method 1: Ring Closure of 2 Pyridinium Substituted Naphtho 1,4 quinones with Nitromethane 567 28.7.1.1.1.3 Bispyrrolo Fused Quinones and Further Variants 568 28.7.1.1.1.3.1 Method 1: Cyclocondensation at Indolequinone 568 28.7.1.1.1.3.2 Method 2: Diels Alder Reaction with Indolequinones 569 28.7.1.1.1.3.3 Method 3: Double Cyclization of 2,5 Bis(arylamino) 3,6 dibromobenzo 1,4 quinones 570 28.7.1.1.1.4 Isoindolequinones 571 28.7.1.1.1.4.1 Method 1: o Dialkynylarene Annulation 571 28.7.1.1.1.4.2 Method 2: Azomethine 1,3 DipolarCycloaddition 572 28.7.1.1.1.5 Benzoxazolequinones 573 28.7.1.1.1.5.1 Method 1: Annulation of a Phenol Followed by Oxidation 573 28.7.1.1.1.6 Benzothiazolequinones 574 28.7.1.1.1.6.1 Method 1: Fremy's Salt Oxidation Followed by Nucleophilic Addition ¦¦¦ 574 28.7.1.1.1.7 Indazolequinones and Benzindazolequinones 576 28.7.1.1.1.7.1 Method 1: Ring Closure Reactions of Substituted Benzoquinones 576 28.7.1.1.1.7.2 Method 2: 1,3 DipolarCycloaddition Reactions with Quinones 577 28.7.1.1.1.8 Benzimidazolequinones 578 28.7.1.1.1.8.1 Method 1: Oxidation Reactions 578 28.7.1.1.1.9 Benzotriazolequinones 580 28.7.1.1.1.9.1 Method 1: 1,3 DipolarCycloaddition of p Quinones with Sodium Azide 580 28.7.1.1.1.10 Quinolinequinones, Isoquinolinequinones, and Higher Analogues 581 28.7.1.1.1.10.1 Method 1: Ring Closure Reactions of Substituted Benzoquinones 581 28.7.1.1.1.10.2 Method 2: Intramolecular Acid Catalyzed Cyclization of 2 [(2 Acetylaryl)amino]benzo 1,4 quinones 581 28.7.1.1.1.10.3 Method 3: Aza Diels Alder Reactions 582 XXXII Table of Contents 28.7.1.1.1.11 Isoquinolinequinones 583 28.7.1.1.1.11.1 Method 1: Oxidative Demethylation 583 28.7.1.1.1.11.2 Method 2: Ring Expansion of Cyclobutenone Derivatives Followed by Oxidation 584 28.7.1.1.1.12 Quinoxaline and Quinazolinequinones 585 28.7.1.1.1.12.1 Method 1: Oxidative Demethylation or Oxidation with Ammonium Cerium(IV) Nitrate 585 28.7.1.1.1.12.2 Method 2: Classical Annulation of 2,5 Dimethoxybenzaldehyde 587 28.7.1.1.2 Nitrogen Containing Hetarene o Quinones 587 28.7.1.1.2.1 Indolequinones 587 28.7.1.1.2.1.1 Method 1: Thermolysis of a 3 Azido 4 styrylbenzo 1,2 quinone 587 28.7.1.1.2.1.2 Method 2: Oxidation 588 28.7.1.1.2.2 o Quinones of Quinolines and Isoquinolines 588 28.7.1.1.2.2.1 Method 1: Fremy's Salt Oxidation 589 28.7.2 Product Subclass 2: Oxygen and Sulfur Containing Hetarene Quinones A. C. Criesbeck 28.7.2 Product Subclass 2: Oxygen and Sulfur Containing Hetarene Quinones 593 28.7.2.1 Synthesis of Product Subclass 2 594 28.7.2.1.1 Benzofuranquinones, Benzothiophenequinones, and Higher Annulated Analogues 594 28.7.2.1.1.1 Method 1: Oxidation of Benzofurans 595 28.7.2.1.1.1.1 Variation 1: Oxidation with Fremy's Salt 595 28.7.2.1.1.1.2 Variation 2: Oxidation with Chromium Reagents 597 28.7.2.1.1.1.3 Variation 3: Oxidation with Other Reagents 597 28.7.2.1.1.2 Method 2: Ring Closure Reactions of Furans 598 28.7.2.1.1.2.1 Variation 1: Furan Metalation and Cyclization 598 28.7.2.1.1.2.2 Variation 2: Fischer Carbene Reactions (Dotz Benzannulation) 598 28.7.2.1.1.2.3 Variation 3: Intramolecular Friedel Crafts Acylation 600 28.7.2.1.1.3 Method 3: Ring Closure Reactions of Quinones 601 28.7.2.1.1.3.1 Variation 1: Ullmann Reaction of Benzoquinones 601 28.7.2.1.1.3.2 Variation 2: Dehydration of Hydroxylated Quinones 601 28.7.2.1.1.3.3 Variation 3: Nucleophilic Addition of Hydroxyaryl Substituted Quinones 602 28.7.2.1.1.3.4 Variation 4: Intramolecular Nucleophilic Substitution 602 28.7.2.1.1.3.5 Variation 5: Oxidative Cyclization by Mercury(ll) Acetate and 3 Chloroperoxybenzoic Acid 603 28.7.2.1.1.4 Method 4: Ring Annulation of Quinones 604 28.7.2.1.1.4.1 Variation 1: Michael Addition and Subsequent Cyclization of CH Active Methylene Compounds 604 28.7.2.1.1.4.2 Variation 2: Michael Addition and Subsequent Cyclization of Phenols — 604 28.7.2.1.1.4.3 Variation 3: Addition of Enamines and Vinyl Sulfides 605 Table of Contents XXXIII 28.7.2.1.1.4.4 Variation 4: Photochemical Addition of Alkenes and Alkynes to Quinones 606 28.7.2.1.1.4.5 Variation 5: Palladium Catalyzed Coupling and Ring Closure of Phenyliodonium Betaines 607 28.7.2.1.1.4.6 Variation 6: Diels Alder Cycloaddition 607 28.7.2.1.1.5 Method 5: Ring Closure Reactions of Bi(quinones) 608 28.7.2.1.1.5.1 Variation 1: Acid and Base Induced Ring Closure 608 28.7.2.1.1.5.2 Variation 2: Thermal and Photochemical Ring Closure 609 28.7.2.1.1.6 Method 6: Ring Enlargement of Cyclobutenones 609 28.7.2.1.1.7 Method 7: Modification of Benzo[b]furanquinones 611 28.7.2.1.1.7.1 Variation 1: Diels Alder Reactions 611 28.7.2.1.1.7.2 Variation 2: Hetero Diels Alder Reactions 613 28.7.2.1.1.7.3 Variation 3: Palladium Catalyzed Coupling of Boronates 613 28.7.2.1.2 Benzo[c]furanquinones 614 28.7.2.1.3 Pyranbenzoquinones and Pyrannaphthoquinones 614 28.7.2.1.4 Benzothiophenequinones 614 28.7.2.1.4.1 Method 1: Oxidation of Benzo[b]thiophene Derivatives 615 28.7.2.1.4.2 Method 2: Intramolecular Condensation of Thiophenecarboxylates 615 28.7.2.1.4.2.1 Variation 1: Using Thiophenecarboxylates 615 28.7.2.1.4.2.2 Variation 2: Using Benzoic Acid Derivatives 616 28.7.2.1.4.3 Method 3: Thiophene Metalation and Tandem Nucleophilic Addition ¦•¦ 616 28.7.2.1.4.4 Method 4: Tandem Conjugate Addition and Cyclization 616 28.7.2.1.4.5 Method 5: Intra and Intermolecular Friedel Crafts Acylations 617 28.8 Product Class 8: Sulfur Analogues of Quinones M. Yoshifuji and S. Kawasaki 28.8 Product Class 8: Sulfur Analogues of Quinones 623 28.8.1 Product Subclass 1: p Monothioquinones 623 28.8.1.1 Synthesis of Product Subclass 1 623 28.8.2 Product Subclass 2: o Monothioquinones 626 28.8.21 Synthesis of Product Subclass 2 626 28.8.3 Product Subclass 3: Dithioquinones 627 28*3.1 Synthesis of Product Subclass 3 627 28.9 Product Class 9: Benzo 1,2 , Benzo 1,4 , Naphtho 1,2 , and Naphtho 1,4 quinone Imines and Diimines M. C. Carrefio and M. Ribagorda 28.9 Product Class 9: Benzo 1,2 , Benzo 1,4 , Naphtho 1,2 , and Naphtho 1,4 quinone Imines and Diimines 629 28.9.1 Product Subclass 1: Benzoquinone Imines and Diimines 630 28^.1.1 Synthesis of Product Subclass 1 630 28.9.1.1.1 Method 1: Oxidation of Anilines and Benzenediamines 630 XXXIV Table of Contents 28.9.1.1.1.1 Variation 1: Using Lead(IV) Acetate 630 28.9.1.1.1.2 Variation 2: Using Hypohalites 635 28.9.1.1.1.3 Variation 3: Using Silver(l) Oxide 638 28.9.1.1.1.4 Variation 4: Using Iron(lll) Chloride 640 28.9.1.1.1.5 Variation 5: Using Manganese(IV) Oxide 642 28.9.1.1.1.6 Variation 6: Using Hypervalent Iodine Reagents 644 28.9.1.1.1.7 Variation 7: Using Peroxides 645 28.9.1.1.1.8 Variation 8: Using Cobalt Mediated Catalytic Oxidation by Oxygen 646 283.1.1.1.9 Variation 9: Using Fremy's Salt 647 28.9.1.1.1.10 Variation 10: Using Ammonium Cerium(IV) Nitrate 647 28.9.1.1.1.11 Variation 11: Oxidative Coupling of Phenols and Anilines with Amines — 647 28.9.1.1.1.12 Variation 12: Electrooxidation 649 28.9.1.1.2 Method 2: Condensation of Quinone Derivatives with Amines 658 28.9.1.1.2.1 Variation 1: Intermolecular Processes 658 28.9.1.1.2.2 Variation 2: Intramolecular Processes 663 28.9.1.1.3 Method 3: Transition Metal Quinone Diimine Synthesis 667 28.9.1.1.4 Method 4: Organometallic C—N Coupling from N Chloroquinone Imines 669 283.1.2 Applications of Product Subclass 1 in Organic Synthesis 670 28.9.1.2.1 Method 1: Diels Alder Reactions 670 28.9.1.2.1.1 Variation 1: Cycloaddition Reactions of Benzo 1,2 quinone Imines 670 28.9.1.2.1.2 Variation 2: Cycloaddition Reactions of Benzo 1,4 quinone Imines 673 28.9.1.2.2 Method 2: Dipolar Cycloadditions 681 283.1.2.3 Method 3: Reactions with Alkenes Promoted by Lewis Acids 682 28.9.1.2.4 Method 4: 1,4 Addition Reactions 695 28.9.2 Product Subclass 2: Naphthoquinone Imines and Diimines 706 28.9.2.1 Synthesis of Product Subclass 2 706 28.9.2.1.1 Method 1: Oxidative Coupling of Naphthols with Amines 706 28.9.2.1.2 Method 2: Oxidative Coupling of 1 Naphthylcyanamide with Anilines ••• 710 28.9.2.1.3 Method 3: Substitutions on Naphthoquinones with Amines 712 283.2.1.3.1 Variation 1: Substitution of Sulfonic Groups 712 28.9.2.1.3.2 Variation 2: Substitution of Methoxy Groups 714 283.2.1.4 Method 4: Condensation of Naphthoquinones with Amines 714 28.9.2.1.5 Method 5: Condensation of Naphthoquinones with /V Sulfinylarylamines 716 283.2.1.6 Method 6: Reactions of Naphthoquinones with N Phenyliminophosphoranes 717 283.2.1.7 Method 7: Oxidation of Aminonaphthols, Naphthalenediamines, and Naphthylamines 718 283.2.1.8 Method 8: Diels Alder Reactions of Isoindoles with Activated Acetylene Derivatives 721 283.2.1.9 Method 9: Synthesis and Oxidation of N Hydroxy N phenyl naphthalen 1 amines 722 283.2.1.10 Method 10: Reactions of Naphthoquinones with Bis(trimethylsilyl)carbodiimide 723 283.2.2 Applications of Product Subclass 2 in Organic Synthesis 724 283.2.2.1 Method 1: Halogenation 724 283.2.2.2 Method 2: [3 + 2] Photoaddition with Alkenes 726 Table of Contents XXXV 28.9.2.2.3 Method 3: 1,4 Addition Aromatization 726 28.9.2.2.4 Method 4: Oxidative Coupling 729 28.9.2.2.5 Method 5: The Imino Group as Nucleophile 729 28.10 Product Class 10: Anthraquinone and Phenanthrenedione Imines and Diimines C. Avendano and J. C. Menendez 28.10 Product Class 10: Anthraquinone and Phenanthrenedione Imines and Diimines 735 28.10.1 Product Subclass 1:Anthra 9,10 quinone Imines and Diimines 739 28.io.li Synthesis of Product Subclass 1 739 28.10.1.1.1 Ring Annulation or Ring Closure Reactions 739 28.10.1.1.1.1 Method 1: Diels Alder Reactions of Naphthoquinone Imines 739 28.10.1.1.1.2 Method 2: Oxidative Photochemical Cyclization of 9 (2 lodoanilino) 4,5 phenanthrolin 10 ols 740 28.10.1.1.1.3 Method 3: Intramolecular Friedel Crafts Acylation of 1 (2 Carboxyphenyl)isoquinolines 741 28.10.1.1.1.4 Method 4: Intramolecular Friedel Crafts Acylation of 10 Hetaryl 2,9 phenanthridine 1 carbonitriles 741 28.10.1.1.1.5 Method 5: Intramolecular Cyclization of 2,2' Bis(phthalimido)biphenyls 742 28.10.1.1.1.6 Method 6: Double Cyclization of 3 [(2 Arylethyl)amino] benzo[c]furan 1(3H) one 743 28.10.1.1.1.7 Method 7: Hydrolytic Cyclization of N (3 {2 [(5,8 Dioxo 5,8 dihydro quinolin 6 yl)amino]phenyl} 3 oxopropyl) 2,2,2 trifluoro acetamide 744 28.10.1.1.2 Creation of the Quinone Imine Functionality on a Preexisting Six Membered Ring 745 28.10.1.1.2.1 Method 1: Oxidation of N Arylanthracen 9 amines, Tetracen 5 amines, or Azaviolanthrenes 745 28.10.1.1.2.2 Method 2: Photonitrosation of 9 Anthrol 748 28.10.1.1.2.3 Method 3: Palladium Catalyzed Amination/Oxidation of 9 Bromoanthracenes 749 28.10.1.1.2.4 Method 4: Oxidative Amination of 9 Anthrones 750 28.10.1.1.2.5 Method 5: Oxidation of 10 Amino 9 anthrols 750 28.10.1.1.2.6 Method 6: Condensation of 9 Anthrones with Nitrosoarenes 751 28.10.1.1.2.7 Method 7: Reactions of 10,10 Dibromo 9 anthrones with Nitrogen Containing Nucleophiles 752 28.10.1.1.2.8 Method 8: Nitrosation of Anthracen 9 amine 752 28.10.1.1.2.9 Method 9: Diazocoupling of 9 Anthrones 753 28.10.1.1.2.10 Method 10: Decomposition of 10 Azido 9 anthrones 754 28.10.1.1.2.11 Method 11: Condensation of Anthra 9,10 quinones or Anthra 9,10 quinone Acetals with Ammonia or Amines 754 28.10.1.1.2.12 Method 12: Condensation of 1 Aminoanthra 9,10 quinones with Amides, Amidines, or Nitriles 756 XXXVI Table of Contents 28.10.1.1.2.13 Method 13: Intramolecular Condensations of Anthra 9,10 quinones with Masked Amino Croups 757 28.10.1.1.2.14 Method 14: Reactionsof Anthra 9,10 quinones with Aryliminodimagnesium Reagents 759 28.10.1.1.2.15 Method 15: Reactions of Anthraquinones with Bis(trimethylsilyl)carbodiimide 760 28.10.1.1.2.16 Method 16: Intramolecular Cyclization of 1 (Cyanomethyl) or 1 (Carbamoylmethyl)anthra 9,10 quinones 761 28.10.1.1.2.17 Method 17: Reactions of 9 Aryloxyanthra 1,10 quinones with Amines ••• 761 28.10.1.1.2.18 Method 18: Reactionsof 1 [2 (Dimethylamino)vinyl]azanthraquinones with Ammonia 762 28.10.1.1.2.19 Method 19: Self Coupling of 1 Aminoanthra 9,10 quinones 763 28.10.1.1.2.20 Method 20: Reactions of 1 Substituted Anthra 9,10 quinones with Nucleophiles 764 28.10.1.1.2.20.1 Variation 1: Reactionsof 1 Haloanthra 9,10 quinones with Hydrazine or 2 Aminobenzenethiol 764 28.10.1.1.2.20.2 Variation 2: Reactionsof 1 Alk 1 ynylanthra 9,10 quinoneswith Hydrazines 765 28.10.1.1.2.21 Method 21: Copper Catalyzed Reactions of 1 Haloanthra 9,10 quinones with Amidines, Guanidines, and Related Compounds 766 28.10.1.1.2.22 Method 22: Synthesis from Anthracenes and Anthracene Diones Bearing a Nitrogen Containing Croup or Groups 767 28.10.1.1.2.22.1 Variation 1: Hydrolysis of Anthra 9,10 quinone Diimines to Monoimines 767 28.10.1.1.2.22.2 Variation 2: Dipolar Cycloadditions between Quinomethanes and Azides, and Diazoalkane Extrusion 768 28.10.1.1.2.22.3 Variation 3: Transformations of Anthra 9,10 quinone Imines and Hydrazones 769 28.10.1.1.2.22.4 Variation 4: Transformations of Anthra 9,10 quinone Oximes 769 28.10.1.1.2.22.5 Variation 5: Reactionsof 10 Diazoanthracen 9(10H) ones with Nitrogen Containing Electrophiles 770 28.10.1.1.2.22.6 Variation 6: ReductiveTautomerization of Anthra 1,4 quinone Imines ••¦ 771 28.10.2 Product Subclass 2: Anthra 1,2 quinone and Anthra 1,4 quinone Imines and Diimines 771 28.10.21 Synthesis of Product Subclass 2 771 28.10.2.1.1 Ring Closure Reactions 771 28.10.2.1.1.1 Method 1: Oxidative Coupling of 1 Phenyl 2,3 bis(pyrimidin 5 yl) benzenes 771 28.10.2.1.1.2 Method 2: Cycloaddition of Homophthalic Anhydrides and Benzo 1,4 quinone Imines and Subsequent Oxidation 772 28.10.2.1.2 Creation of the Quinone Imine Functionality on a Preexisting Six Membered Ring 774 28.10.2.1.2.1 Method 1: Oxidation of 1 (Acylamino) 2 anthrols 774 28.10.2.1.2.2 Method 2: Oxidation of Anthracenamines and Their Derivatives 774 28.10.2.1.2.3 Method 3: Rearrangement of 4 Aryloxyanthracen 1 amines and Related Compounds 775 Table of Contents XXXVII 28.10.2.1.2.4 Method 4: Condensation of Anthra 9,10 quinone Diamines and Anthracenamines with Carbonyl Compounds 777 28.10.2.1.2.5 Method 5: Condensation of Anthra 1,2 quinones with Hydrazines 778 28.10.3 Product Subclass 3: Phenanthrene 9,10 dione Imines and Diimines 779 28.io.3i Synthesis of Product Subclass 3 779 28.10.3.1.1 Ring Closure Reactions 779 28.10.3.1.1.1 Method 1: Transannular Cyclizations of [22]Metacyclophanes with N Bromosuccinimide 780 28.10.3.1.1.2 Method 2: Metal Induced Oxidative Intramolecular Aryl Aryl Coupling 780 28.10.3.1.1.3 Method 3: Synthesis of Oxoaporphine Alkaloids by Aryl Aryl Coupling 782 28.10.3.1.1.4 Method 4: PschorrCyclization of 1 (2 Aminobenzyl)isoquinolines 784 28.10.3.1.1.5 Method 5: Oxidative Cyclization of Bisarylhydrazones 785 28.10.31 2 Creation of the Quinone Imine Functionality on a Preexisting Six Membered Ring 787 28.10.3.1.2.1 Method 1: Reaction of Phenanthrene 9,10 diones with Nucleophiles ••• 787 28.10.3.1.2.1.1 Variationi: Reactions with 1,2 Diamines 787 28.10.3.1.2.1.2 Variation 2: Condensation of Phenanthrene 9,10 diones with Hydroxylamine or Sodium Hexamethyldisilazanide 789 28.10.3.1.2.1.3 Variation 3: Condensation of Phenanthrene 9,10 diones with Imino hydrazides, Sulfanamide, Thiosemicarbazide, Semicarbazide, or Aminoguanidines 790 28.10.3.1.2.1.4 Variation 4: Condensation of Phenanthrene 9,10 diones with S Alkylisothiosemicarbazides and Related Compounds 791 28.10.3.1.2.1.5 Variation 5: Reductive Condensation of Phenanthrene 9,10 diones with Aromatic Nitroso or Nitro Compounds 793 28.10.3.1.2.2 Method 2: Condensation of Phenanthrene 9,10 diamines with a Dicarbonyl Compounds 793 28.10.3.1.2.3 Method 3: Condensation of Phenanthrene 9,10 diamines with Bis(methyloximes) 794 28.10.3.1.2.4 Method 4: Reactions of Phenanthrene 9,10 diamines with a Nitro Ketones 795 28.10.3.1.2.5 Method 5: Condensation of Phenanthrene 3,9 diones with 1,2 Diamines 796 28.10.3.1.2.6 Method 6: Condensation of 9 Nitrophenanthrenes with Anilines 797 28.10.3.1.2.7 Method 7: Condensation of lminophenanthren 9(10H) ones with Amines 797 28.10.3.1.2.8 Method 8: Reaction of Phenanthrene 9,10 diones with Arsinimines 798 28.10.3.1.2.9 Method 9: Condensation of Phenanthrene 9,10 dione Monooxime with 1,1 Diarylalkenes 799 28.10.3.1.2.10 Method 10: Condensation of Phenanthrene 9,10 dione Diimines or Dioximeswithgem Dihalides 800 28.10.3.1.2.11 Method 11: Reaction of Phenanthrene with Trithiazyl Trichloride 801 28.10.3.1.2.12 Method 12: Ring Expansion of Phenanthro[9,10 d][1,2,3]triazoles or Phenanthro[9,10 c][1,2,5]oxadiazoles 801 XXXVIII Table of Contents _ 28.11 Product Class 11: Quinone Diazides A. C. Griesbeck and E. Zimmermann 28.11 Product Class 11: Quinone Diazides 807 28.11.1 Synthesis of Product Class 11 809 28.11.1.1 Method 1: Diazotization of Amino Substituted Aromatic Alcohols 810 28.11.1.1.1 Variation 1: Diazotization in Aqueous Media 810 28.11.1.1.2 Variation 2: Diazotization in Organic Solvents 812 28.11.1.1.3 Variation 3: Nitration of Substituted Anilines 816 28.11.1.2 Method 2: Aromatic Substitution of Diazonium Salts 818 28.11.1.2.1 Variation 1: Hydrolysis of 2 or 4 Substituted Diazonium Salts 818 28.11.1.2.2 Variation 2: Elimination of HX from Diazonium Salts 819 28.11.1.2.3 Variation 3: Aromatic Substitution of Aryl Fluorides 820 28.11.1.3 Method 3: Oxidation of Arenediazonium Cations 821 28.11.1.4 Method 4: o or p Nitrosylation of Phenols 821 28.11.1.5 Method 5: Formation of Tosylhydrazones from Quinones 822 28.11.1 6 Method 6: Electrophilic Substitution of Quinone Diazides 823 28.11.1.7 Method 7: Diazo Croup Transfer Reactions 823 28.11.1.8 Methods 8: Additional Methods 825 28.11.2 Applications of Product Class 11 in Organic Synthesis 825 28.11.2.1 Method 1: The Sus Reaction 825 28.11.2.2 Method 2: Application in Photolithographic Processes 827 28.12 Product Class 12: Quinomethanes 28.12.1 Product Subclass 1: o Quinomethanes T. R. R. Pettus and C. Selenski 28.12.1 Product Subclass 1: o Quinomethanes 831 28.12.11 Synthesis of Product Subclass 1 835 28.12.1.1.1 Quinone Enolization 835 28.12.1.1.1.1 Methodi: Heat Assisted Quinone Enolization 835 28.12.1.1.1.2 Method 2: Base Assisted Quinone Enolization 836 28.12.1.1.1.2.1 Variation 1: Using Lithium Methoxide 836 28.12.1.1.1.2.2 Variation 2: Using Sodium Methanethiolate 837 28.12.1.1.1.2.3 Variation 3: Using Amines 838 28.12.1.1.1.3 Method 3: Photochemically Assisted Quinone Enolization 839 28.12.1.1.2 Oxidation 840 28.12.1.1.2.1 Methodi: Oxidation Using Silver(l) Oxide 840 28.12.1.1.3 Extrusions and Retrocycloadditions 843 28.12.1.1.3.1 Method 1: Nucleophilic Displacement 843 28.12.1.1.3.2 Method 2: Mannich Base Precursors 843 Table of Contents XXXIX 28.12.1.1.3.2.1 Variation 1: Thermal Induction 844 28.12.1.1.3.2.2 Variation 2: Quaternization 846 28.12.1.1.3.3 Method 3: 2 (1H Benzotriazol 1 ylmethyl)phenol Precursors 847 28.12.1.1.3.3.1 Variation 1: Basic Conditions 848 28.12.1.1.3.3.2 Variation 2: Thermal Conditions 849 28.12.1.1.3.4 Method 4: 4H 1,2 Benzoxazine Precursors (Thermal Extrusion) 851 28.12.1.1.3.5 Method 5: 2 (fert Butoxycarbonyloxy)benzaldehyde and 2 (tert Butoxy carbonyloxy)benzyl Alcohol Precursors (Basic Conditions) ¦•• 852 28.12.1.1.3.6 Method 6: 2 (Hydroxymethyl)phenol Precursors 858 28.12.1.1.3.6.1 Variation 1: Thermal Induction 858 28.12.1.1.3.6.2 Variation 2: Derivatization of the 2 (Hydroxymethyl)phenol Precursor ••¦ 860 28.12.1.1.3.6.3 Variation 3: Photochemical Induction 860 28.12.1.1.3.6.4 Variation 4: Lewis Acid Induction 861 28.12.1.1.3.6.5 Variation 5: Lewis Base Induction 862 28.12.1.1.3.7 Method 7: 2 Phenylbenzodioxaborin Precursors 863 28.12.1.1.3.7.1 Variation 1: Lewis Acid Induction 864 28.12.1.1.3.8 Method 8: 2 (Halomethyl)phenol Precursors 866 28.12.1.1.3.8.1 Variation 1: Neutral Conditions 867 28.12.1.1.3.8.2 Variation 2: Basic Conditions 867 28.12.1.1.3.8.3 Variation 3: Lewis Acidic Conditions 868 28.12.2 Product Subclass 2: p Quinomethanes A. G. Griesbeck 28.12.2 Product Subclass 2: p Quinomethanes 873 28.i2.2i Synthesis of Product Subclass 2 874 28.12.2.1.1 Method 1: Oxidation of 4 Substituted Phenols 876 28.12.2.1.1.1 Variation 1: Using Silver(l), Lead(IV), or Manganese(IV) Oxide 876 28.12.2.1.1.2 Variation 2: Using Potassium Hexacyanoferrate(lll) 877 28.12.2.1.1.3 Variation 3: Using Other Oxidants 877 28.12.2.1.2 Method 2: Dehydration of 4 (Hydroxyalkyl) and 4 (Hydroxyalkyl)phenyl Substituted Phenols 879 28.12.2.1.2.1 Variation 1: Thermal Dehydration of 4 (Hydroxyalkyl) Substituted Phenols 879 28.12.2.1.2.2 Variation 2: Acid Catalyzed Dehydration of 4 (Hydroxyalkyl) Substituted Phenols 879 28.12.2.1.2.3 Variation 3: Dehydration of 4 (Hydroxyalkyl) Substituted Phenols Using Lithium Aluminum Hydride 879 28.12.2.1.3 Method 3: Dehydrohalogenation of 4 Halomethyl Substituted Phenols 880 28.12.2.1.3.1 Variation 1: Using Amine Bases 880 28.12.2.1.3.2 Variation 2: Using Weak Bases in Aqueous Media 881 28.12.2.1.3.3 Variation 3: Using Metal Alkoxides 881 28.12.2.1.4 Method 4: Acid Catalyzed Dehydration of 4 Methoxyphenyl Substituted Alcohols 882 28.12.2.1.5 Method 5: Elimination of Chloromethane from 4 Chloroalkyl Substituted Anisoles 882 28.12.2.1.6 Method 6: Acid Elimination from 4 (Acyloxy)alkyl Substituted Phenols 883 XL Table of Contents 28.12.2.1.7 Method 7: Decomplexation of Quinomethanes from re Palladium Complexes 884 28.12.2 1.8 Method 8: Condensation of Phenols with Alkyl or Acyl Halides 884 28.12.2.1.8.1 Variation 1: Thermal Condensation 885 28.12.2.1.8.2 Variation 2: Lewis Acid Catalyzed Condensation 885 28.12.2.1.9 Method 9: Reaction of Phenols with Carbenium Ions 885 28.i2.2i.io Method 10: Reaction of Aryl Carbanions with Carbonyl Compounds — 886 28.12.2.1.10.1 Variation 1: Reaction of Metalated Phenols with Carbonyl Compounds 886 28.12.2.1.10.2 Variation 2: Reaction of Metalated Arenes with 4 Acylphenols 887 28.12.2.1.11 Method 11: Oxidation of Phenols to p Diphenoquinones 888 28.12.2.1.12 Method 12: Ring Closure Reactions 888 28.12.2.1.13 Method 13: Addition of Nudeophiles to o Quinones 889 28.12.2.1.14 Method 14: Addition of Nudeophiles to p Quinones 890 28.i2.2i.i5 Method 15: Knoevenagel Addition to p Quinones 890 28.12.2.1.16 Method 16: Wittig Reaction of p Quinones 891 28.12.2.1.17 Method 17: Ketene Additions to p Quinones 893 28.i2.2i.i8 Method 18: Photochemical Addition of Alkynes to p Quinones 893 28.12.2.1.19 Method 19: Modification of p Quinomethanes 894 28.12.2.1.20 Method 20: Condensation of Carbonyl Compounds with Anthrones — 894 28.12.2.1.21 Method 21: Oxidation of Nitrobenzylic Carbanions 895 Keyword Index 901 Author Index 949 Abbreviations 1001
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author	Avendaño, C.
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author_facet	Avendaño, C. Griesbeck, Axel G.
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id	DE-604.BV021661431
illustrated	Illustrated
index_date	2024-07-02T15:06:08Z
indexdate	2024-08-20T00:15:10Z
institution	BVB
isbn	3131187913 1588904601 9783131187918
language	English
oai_aleph_id	oai:aleph.bib-bvb.de:BVB01-014875927
oclc_num	634482094
open_access_boolean
owner	DE-20 DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-210 DE-91G DE-BY-TUM DE-188 DE-11
owner_facet	DE-20 DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-210 DE-91G DE-BY-TUM DE-188 DE-11
physical	XL, 1006 Seiten Illustrationen 26 cm
publishDate	2006
publishDateSearch	2006
publishDateSort	2006
publisher	Thieme
record_format	marc
spelling	Avendaño, C. aut Science of synthesis Houben-Weyl methods of molecular transformations 28 = Category 4, Compounds with two carbon-heteroatom bonds Quinones and heteroatom analogues ed. board: D. Bellus ... Stuttgart [u.a.] Thieme 2006 XL, 1006 Seiten Illustrationen 26 cm txt rdacontent n rdamedia nc rdacarrier Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Chinone (DE-588)4147707-8 gnd rswk-swf Chinone (DE-588)4147707-8 s Chemische Synthese (DE-588)4133806-6 s DE-604 Bellus, Daniel Sonstige oth Griesbeck, Axel G. (DE-588)1029929874 edt Houben, Josef 1875-1940 Sonstige (DE-588)117013870 oth (DE-604)BV013247070 28 Erscheint auch als Online-Ausgabe 978-3-13-183811-7 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014875927&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Science of synthesis Houben-Weyl methods of molecular transformations Chemische Synthese (DE-588)4133806-6 gnd Chinone (DE-588)4147707-8 gnd Avendaño, C.
subject_GND	(DE-588)4133806-6 (DE-588)4147707-8
title	Science of synthesis Houben-Weyl methods of molecular transformations
title_auth	Science of synthesis Houben-Weyl methods of molecular transformations
title_exact_search	Science of synthesis Houben-Weyl methods of molecular transformations
title_exact_search_txtP	Science of synthesis Houben-Weyl methods of molecular transformations
title_full	Science of synthesis Houben-Weyl methods of molecular transformations 28 = Category 4, Compounds with two carbon-heteroatom bonds Quinones and heteroatom analogues ed. board: D. Bellus ...
title_fullStr	Science of synthesis Houben-Weyl methods of molecular transformations 28 = Category 4, Compounds with two carbon-heteroatom bonds Quinones and heteroatom analogues ed. board: D. Bellus ...
title_full_unstemmed	Science of synthesis Houben-Weyl methods of molecular transformations 28 = Category 4, Compounds with two carbon-heteroatom bonds Quinones and heteroatom analogues ed. board: D. Bellus ...
title_short	Science of synthesis
title_sort	science of synthesis houben weyl methods of molecular transformations quinones and heteroatom analogues
title_sub	Houben-Weyl methods of molecular transformations
topic	Chemische Synthese (DE-588)4133806-6 gnd Chinone (DE-588)4147707-8 gnd
topic_facet	Chemische Synthese Chinone
url	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014875927&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
volume_link	(DE-604)BV013247070
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