Science of synthesis: Houben-Weyl methods of molecular transformations 38 = Category 5, Compounds with one saturated carbon-heteroatom bond Peroxides
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| Format: | Book |
| Language: | English |
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Stuttgart [u.a.]
Thieme
2009
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| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XXV, 582 Seiten Illustrationen 26 cm |
| ISBN: | 9783131189110 9781588905291 |
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| 020 | |a 9783131189110 |9 978-3-13-118911-0 | ||
| 020 | |a 9781588905291 |9 978-1-58890-529-1 | ||
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| 041 | 0 | |a eng | |
| 049 | |a DE-355 |a DE-19 |a DE-210 |a DE-91G |a DE-11 | ||
| 100 | 1 | |a Berkessel, Albrecht |e Verfasser |0 (DE-588)1206253118 |4 aut | |
| 245 | 1 | 0 | |a Science of synthesis |b Houben-Weyl methods of molecular transformations |n 38 = Category 5, Compounds with one saturated carbon-heteroatom bond |p Peroxides |c ed. board: D. Bellus ... |
| 264 | 1 | |a Stuttgart [u.a.] |b Thieme |c 2009 | |
| 300 | |a XXV, 582 Seiten |b Illustrationen |c 26 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 700 | 1 | |a Bellus, Daniel |e Sonstige |4 oth | |
| 700 | 1 | |a Alberti, M. N. |4 edt | |
| 700 | 1 | |a Houben, Josef |d 1875-1940 |e Sonstige |0 (DE-588)117013870 |4 oth | |
| 773 | 0 | 8 | |w (DE-604)BV013247070 |g 38 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe |z 978-3-13-183931-2 |
| 856 | 4 | 2 | |m HBZ Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017046319&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-017046319 | |
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Titel: Bd. 38. Science of synthesis. Peroxides
Autor:
Jahr: 2009
Table of Contents
Introduction
A. Berkessel
Introduction 1
38.1 Product Class 1: Alkyl and Cycloalkyl Hydroperoxides
A. Scarso and G. Strukul
38.1 Product Class 1: Alkyl and Cycloalkyl Hydroperoxides 9
38.1 .i Product Subclass 1: a-Unsubstituted Alkyl Hydroperoxides 9
38.1.1.1 Synthesis of Product Subclass 1 10
38.1.1.1.1 Method 1: Reactions of Alkanes with Molecular Oxygen 10
38.1.1.1.2 Method 2: Hydrolysis of Alkyl Metal and
Alkyl Metalloid Peroxides 11
38.1.1.1.2.1 Variation 1: Via Oxidation of Alkylmagnesium Halides with
Molecular Oxygen 11
38.1.1.1.2.2 Variation 2: Via Oxidation of Alkylboron Halides with
Molecular Oxygen 12
38.1.1.1.3 Method 3: Reaction ofOxetaneswith Hydrogen Peroxide 13
38.1.1.1.4 Method4: Reaction of Epoxides with Hydrogen Peroxide 14
38.1.1.1.4.1 Variation 1: Catalyzed by Methyltrioctylammonium
Tetrakis(oxodiperoxotungsto)phosphate 15
38.1.1.1.5 Method 5: Reaction of Alkyl Halides 16
38.1.1.1.5.1 Variation 1: With Hydrogen Peroxide in the Presence of
Silver(l)Trifluoroacetate 16
38.1.1.1.5.2 Variation 2: With 2-Alkoxypropan-2-yl and
2-(2-Methoxyethoxy)propan-2-yl Hydroperoxides 17
38.1.1.1.5.3 Variation 3: With Potassium Superoxide 18
38.1.1.1.6 Method 6: Reaction of Alcohols with Hydrogen Peroxide 19
38.1.1.1.6.1 Variations Without Catalysts 19
38.1.1.1.6.2 Variation 2: With Acid Catalysis 20
38.1.1.1.7 Method 7: Reaction of Dialkyl Sulfates with
Hydrogen Peroxide 20
38.1.1.1.8 Method 8: Reaction of Alkyl Methanesulfonates with
Hydrogen Peroxide 21
38.1.1.1.8.1 Variation 1: Reaction of Homoallylic Methanesulfonates with
Hydrogen Peroxide 22
38.1.1.1.8.2 Variation 2: Reaction of Cyclic Homoallylic 4-Bromobenzenesulfonates
with Hydrogen Peroxide 23
38.1.1.1.9 Method 9: Reaction of 1-Substituted 1-Sulfonylhydrazineswith
Molecular Oxygen under Basic Conditions 23
38.1.1.1.10 Method 10: Reaction of 1-Alkyl-2-tosylhydrazines with
Hydrogen Peroxide and Sodium Peroxide 24
38.1.1.1.11 Method 11: Synthesis from Alkenes 25
38.1.1.1.11.1 Variation 1: With Triethylsilane and Oxygen with a
Cobalt(II) Catalyst 26
38.1.1.1.11.2 Variation 2: Photooxygenation with Methylene Blue Sensitizer 27
38.1.1.1.11.3 Variation 3: Photooxygenation with 4-Chlorobenzenethiol 28
38.1.1.1.11.4 Variations With N-Bromosuccinimide and
Hydrogen Peroxide 28
38.1.1.1.11.5 Variation 5: With 1,3-Dibromo-5,5-dimethylhydantoinand
Hydrogen Peroxide 29
38.1.1.1.12 Method 12: Synthesis from Conjugated Dienes 30
38.1.1.1.13 Method 13: Synthesis from Peroxy Esters 30
38.1.1.2 Applications of Product Subclass 1 in Organic Synthesis 31
38.1.2 Product Subclass 2: a-Halogen-Substituted Alkyl Hydroperoxides 31
38.1.2.1 Synthesis of Product Subclass 2 32
38.1.2.1.1 ct-Fluoroalkyl Hydroperoxides 32
38.1.2.1.1.1 Method 1: Decomposition of Hexafluoroacetone
Perhydrate 32
38.1.2.1.1.2 Method 2: Reaction of Perfluoroperoxy Derivatives
withWater 32
38.1.2.1.2 ci-Chloroalkyl Hydroperoxides 33
38.1.2.1.2.1 Method 1: Reaction of Chloroalkenes with Ozone 33
38.1.3 Product Subclass 3: a-Oxygen-Substituted Alkyl Hydroperoxides 34
38.1.3.1 Synthesis of Product Subclass 3 34
38.1.3.1.1 ct-Hydroxyalkyl Hydroperoxides 34
38.1.3.1.1.1 Method 1: Reaction of Aldehydes with
Hydrogen Peroxide and Iodine 34
38.1.3.1.1.2 Method 2: Reaction of a-Halo Ketones with
Hydrogen Peroxide 35
38.1.3.1.2 a-Alkoxyalkyl Hydroperoxides 36
38.1.3.1.2.1 Method 1: Ozonolysis of Alkenes 36
38.1.3.1.2.2 Method 2: Reaction of Vinyl Ethers with
Ozone and Alcohols 38
38.1.3.1.2.2.1 Variation 1: With Hydrogen Peroxide 40
38.1.3.1.2.2.2 Variation 2: With Hydrogen Peroxide and Silica Gel 40
38.1.3.1.2.2.3 Variation 3: With Hydrogen Peroxide and
Molybdenum(VI) Oxide 41
38.1.3.1.2.3 Method 3: Reaction of Dialkyl Ethers with
Molecular Oxygen 42
38.1.3.1.2.4 Method4: ci-Reaction of Cyclopropyl Alcohols with
Hydrogen Peroxide 42
38.1.3.1.2.5 Method 5: Reaction of Ketones and Alcohols with
Hydrogen Peroxide 44
38.1.3.1.2.6 Method 6: Reaction of Hydroxy Ketones and Diketones with
Hydrogen Peroxide 44
38.1.3.1.2.7 Method 7: Reaction ofKetoneswith Hydrogen Peroxide
Catalyzed by Iodine 45
38.1.3.1.2.8 Method 8: Reaction of Homoallylic 4-Bromobenzenesulfonates
and Hydrogen Peroxide 46
38.1.3.1.2.9 Method 9: Ring Opening of Oxetanes with
Hydrogen Peroxide 47
38.1.3.1.3 a-Peroxyalkyl Hydroperoxides 47
38.1.3.1.3.1 Method 1: Reaction of Alkenes and Vinyl Ethers with Ozone 47
38.1.3.1.3.1.1 Variation 1: Intramolecular Reaction of Alkyl Hydroperoxides
with Carbonyl Oxides Generated by
Ozonolysis of Alkenes 48
38.1.3.1.3.2 Method 2: Reaction of Ketones with Hydrogen Peroxide 49
38.1.3.1.3.3 Method 3: Reaction of Acetals with Hydrogen Peroxide Mediated
by Boron Trifluoride-Diethyl Ether Complex 49
38.1.3.1.3.4 Method4: Reaction of Dialkyl Ethers with
Molecular Oxygen 50
38.1.3.1.4 ct-(Triorganosiloxy)alkyl Hydroperoxides 51
38.1.3.1.4.1 Method 1: Reaction ofTrialkylsilyl Vinyl Ethers and
Hydrogen Peroxide 51
38.1.3.1.5 ct-(Acyloxy)alkyl Hydroperoxides 51
38.1.3.1.5.1 Method 1: Photooxidation of an Enol Lactone 51
38.1.3.1.6 1,1-Bis(hydroperoxy)alkanes 52
38.1.3.1.6.1 Method 1: Reaction of Ketones with Hydrogen Peroxide
with Acid Catalysts 52
38.1.3.1.6.1.1 Variation 1: With 1,2-Bis(diphenylphosphoryl)ethane 53
38.1.3.1.6.1.2 Variation 2: Catalyzed by Ammonium Cerium(IV) Nitrate 54
38.1.3.1.6.1.3 Variation 3: Catalyzed by Methyltrioxorhenium(VII)
in Trifluoroethanol 55
38.1.3.1.6.1.4 Variation 4: Catalyzed by Molecular Iodine 55
38.1.3.1.6.1.5 Variation5: Catalyzed byTungsticAcid 56
38.1.3.1.6.2 Method 2: Reaction of Tosylhydrazones with
Hydrogen Peroxide 57
38.1.3.1.6.3 Method 3: Reaction of Vinyl Ethers with Ozone and
Hydrogen Peroxide 58
38.1.3.1.6.4 Method 4: Reaction of Ketals with Hydrogen Peroxide 59
38.1.3.1.6.5 Method 5: Ring Opening of Bicyclic Benzyl Alcohols with
Hydrogen Peroxide 60
38.1.3.2 Applications of Product Subclass 3 in Organic Synthesis 60
38.1.4 Product Subclass 4: a-Sulfur-Substituted Alkyl Hydroperoxides 61
38.1.4.1 Synthesis of Product Subclass 4 61
38.1.4.1.1 Method 1: Photooxidation of Thiazolidines with Molecular Oxygen
in the Presence of Tetraphenylphorphyrin 61
38.1.5 Product Subclass 5: a-Nitrogen-Substituted Alkyl Hydroperoxides 61
38.1.5.1 Synthesis of Product Subclass 5 62
38.1.5.1.1 a-Aminoalkyl Hydroperoxides 62
38.1.5.1.1.1 Method 1: Reaction of Carbonyl Compounds with Ammonia or
Amines and Hydrogen Peroxide 62
38.1.5.1.2 (x-(Acylamino)alkyl Hydroperoxides 64
38.1.5.1.2.1 Methodi: Reaction of Cyclic Amides and N-Alkylamides
with Oxygen 64
38.1.5.1.2.2 Method 2: Reaction of N-Heterocycles with
Hydrogen Peroxide 64
38.1.5.1.3 a-Hydrazinoalkyl Hydroperoxides 65
38.1.5.1.3.1 Methodi: Oxidation of Hydrazoalkanes 65
38.1.5.1.4 a-(N-Alkyl-N-nitrosoamino)alkyl Hydroperoxides 65
38.1.5.1.4.1 Method 1: Reaction of Dialkylnitrosamines with
Lithium Diisopropylamide and Oxygen 65
38.1.5.1.4.2 Method 2: Reaction of 1 -Acetoxyalkyl(alkyl)nitrosamines with
Hydrogen Peroxide 66
38.1.5.1.5 4-Hydroperoxy-1,3,2-oxazaphosphorinane2-Oxides 67
38.1.5.1.5.1 Methodi: Reaction of 4-Hydroxy-1,3,2-oxazaphosphorinane
2-Oxides with Hydrogen Peroxide 67
38.1.5.1.5.2 Method 2: Reaction of a Phosphoric Amide Diester Bearing
0- or N-Alkenyl Residues and Ozone 67
38.1.5.2 Applications of Product Subclass 5 in Organic Synthesis 68
38.2 Product Class 2: Allylic Hydroperoxides
U. BergstrafSerand J. Hartung
38.2 Product Class 2: Allylic Hydroperoxides 73
38.2.1 Synthesis of Product Class 2 78
38.2.1.1 Methodi: Synthesis from Alkenes 78
38.2.1.1.1 Variation 1: With Triplet Dioxygen 78
38.2.1.1.2 Variation 2: With Singlet Dioxygen 80
38.2.1.2 Method 2: Synthesis from Arenes 93
38.2.1.2.1 Variation 1: Reaction with Dioxygen under Basic Conditions 93
38.2.1.2.2 Variation 2: Reaction with Triplet Dioxygen in the Presence of
Transition Metal Compounds 95
38.2.1.2.3 Variation 3: Reaction with Singlet Dioxygen 96
38.2.1.3 Method 3: Synthesis from Allylic Halides 98
38.2.1.3.1 Variation 1: Reaction with Hydrogen Peroxide 98
38.2.1.4 Method 4: Synthesis from Allyl Sulfonates 99
38.2.1.4.1 Variation 1: Reaction with Hydrogen Peroxide 99
38.2.1.5 Method 5: Synthesis from Endoperoxides 100
38.2.1.5.1 Variation 1: Reaction with Nucleophiles 100
38.2.1.6 Method 6: Synthesis from Allyl Hydroperoxides 101
38.2.1.6.1 Variation 1: Via Rearrangement 101
38.2.1.6.2 Variation2: Separation of Racematesvia HPLC 102
38.2.1.6.3 Variation 3: Enzymatic Kinetic Resolution of Racemates 103
38.3 Product Class 3: Benzylic Hydroperoxides
J. Hartung and H. Heydt
38.3 Product Class 3: Benzylic Hydroperoxides 109
38.3.1 Synthesis of Product Class 3 110
38.3.1.1 Method 1: Synthesis from Aryl- or Hetarylalkanes with Retention of the
Carbon Skeleton 112
38.3.1.1.1 Variation 1: Autoxidation 112
38.3.1.1.2 Variation 2: Reaction with Dioxygen in the Presence of Metal Ions 117
38.3.1.1.3 Variation 3: Reaction with Dioxygen in the Presence of Bases 118
38.3.1.1.4 Variation 4: Reaction with Dioxygen in the Presence of
N-Hydroxyphthalimide 119
38.3.1.1.5 Variation 5: Reaction with tert-Butyl Hydroperoxide and a
Transition-Metal Catalyst 119
38.3.1.1.6 Variation 6: Reaction with Dioxygen in the Presence of Photochemically
Excited Electron-Transfer Reagents 120
38.3.1.2 Method 2: Synthesis from Arylalkanes in Combination with
C-C Bond Cleavage 121
38.3.1.2.1 Variation 1: Photochemically Induced Reaction 121
38.3.1.3 Method 3: Synthesis from Alkenes 122
38.3.1.3.1 Variation 1: With Triplet Dioxygen in the Presence of Thiols 122
38.3.1.3.2 Variation 2: Reaction with Triplet Dioxygen in the Presence of Cobalt(ll)
Compounds and Silanes 122
38.3.1.3.3 Variation 3: Reaction with Triplet Dioxygen and Boranes 123
38.3.1.3.4 Variation 4: Via Electron-Transfer Processes 124
38.3.1.3.5 Variation 5: Reaction with Singlet Dioxygen 125
38.3.1.3.6 Variation 6: Reaction with Hydrogen Peroxide and Mercury(ll) Salts — 125
38.3.1.4 Method 4: Synthesis from Arenes 126
38.3.1.4.1 Variations From Phenols with Dioxygen in the Absence of Catalysts ••• 126
38.3.1.4.2 Variation 2: Reaction with Singlet Dioxygen 128
38.3.1.5 Method 5: Synthesis from Haloalkanes 129
38.3.1.5.1 Variation 1: With Hydrogen Peroxide under Acidic Conditions 129
38.3.1.5.2 Variation 2: With Hydrogen Peroxide under Basic Conditions 130
38.3.1.6 Method 6: Synthesis from Alcohols 130
38.3.1.6.1 Variation 1: By Reaction with Hydrogen Peroxide under
Acidic Conditions 130
38.3.1.7 Method 7: Synthesis from Carboxylic Acid Esters 131
38.3.1.7.1 Variation 1: Reaction with Hydrogen Peroxide 131
38.3.1.8 Method8: Synthesis from Ethers 132
38.3.1.8.1 Variation 1: Reaction of Acyclic Ethers with Hydrogen Peroxide 132
38.3.1.9 Method 9: Synthesis from Peroxy Esters 133
38.3.1.9.1 Variation 1: Hydrolysis in the Presence of Bis(tributyltin) Oxide 133
38.3.1.10 MethodiO: Synthesis from Other Benzylic Hydroperoxides 133
38.3.1.10.1 Variation 1: Separation of Racemates via HPLC 133
38.3.1.10.2 Variation 2: Kinetic Resolution of Racemates Using
Enantiopure Phosphines 134
38.3.1.10.3 Variation 3: Lipase-Catalyzed Kinetic Resolution of Racemates 134
38.3.1.10.4 Variation 4: Kinetic Resolution of Racemates Using
Native Peroxidases 135
38.3.1.10.5 Variation 5: Enzymatic Kinetic Resolution of Racemates Using a
Semisynthetic Peroxidase 137
38.3.1.10.6 Variation 6: Kinetic Resolution of Racemates Using Microorganisms — 138
38.4 Product Class 4: Salts of Alky I Hydroperoxides
A. Scarso and G. Strukul
38.4 Product Class 4: Salts of Alkyl Hydroperoxides 143
38.4.1 Product Subclass 1: Group 15 Salts of Alkyl Hydroperoxides 144
38.4.1.1 Synthesis of Product Subclass 1 144
38.4.1.1.1 Method 1: Synthesis of (Alkylperoxy)antimony Compounds 144
38.4.2 Product Subclass 2: Croup 14 Salts of Alkyl Hydroperoxides 144
38.4.2.1 Synthesis of Product Subclass 2 145
38.4.2.1.1 Method 1: Synthesis of (Alkylperoxy)silanes 145
38.4.2.1.1.1 Variationi: Reaction of SilylEnol Ethers with Singlet Oxygen 145
38.4.2.1.1.2 Variation 2: Reaction of Chlorotriorganosilanes or
TriorganosilylTrifluoromethanesuIfonates
with Alkyl Hydroperoxides 146
38.4.2.1.1.3 Variation 3: Reaction of A/,0-Bis(triorganosilyl)acetamides with
Alkyl Hydroperoxides 150
38.4.2.1.1.4 Variation 4: Reaction of y-SilylAllylic Alcohols with Ozone 150
38.4.2.1.1.5 Variation 5: Reaction of Alkenes with Oxygen and Triethylsilane
Promoted by Cobalt(ll) Catalysts 151
38.4.2.1.2 Method2: Synthesis of Germanium Alkyl Peroxides 153
38.4.2.1.2.1 Variation 1: Reaction of Halogermanes with Alkyl Hydroperoxides
and Ammonia orTertiary Amines 153
38.4.2.1.3 Method3: SynthesisofTinAlkyl Peroxides 154
38.4.2.1.3.1 Variationi: Reaction of Triorganostannanes with
Alkyl Hydroperoxides 154
38.4.2.1.3.2 Variation 2: Reaction of Hydroxytriorganostannanes or
Oxytriorganostannanes with Alkyl Hydroperoxides 154
38.4.2.1.3.3 Variation 3: Synthesis of 1,3-Bis(alkylperoxy)-1,1,3,3-
tetraorganodistannoxanes and (Alkylperoxy)(chloro)-
1,1,3,3-tetraorganodistannoxanes 155
38.4.3 Product Subclass 3: Croup 13 Salts of Alkyl Hydroperoxides 156
38.4.3.1 Synthesis of Product Subclass 3 156
38.4.3.1.1 Method 1: Synthesis of (Alkylperoxy)boron Compounds 156
38.4.3.1.1.1 Variationi: Reaction ofTrialkylboranes with Oxygen 156
38.4.3.1.1.2 Variation 2: Reaction of Boron Halides with
Alkyl Hydroperoxides 158
38.4.3.1.1.3 Variation 3: Reaction of Tetraacetyl Diborate with
Alkyl Hydroperoxides 158
38.4.3.1.1.4 Variation 4: Reaction of Alkyldichloroboranes orChlorodicyclopentyl-
borane with Molecular Oxygen 159
38.4.3.1.1.5 Variation 5: Oxidation of Trialkylboroxins 159
38.4.3.1.2 Method 2: Synthesis of Aluminum Alkyl Peroxides 160
38.4.3.1.3 Method 3: Synthesis of Indium Alkyl Peroxides 160
38.4.4 Product Subclass 4: Group 2 Salts of Alkyl Hydroperoxides 161
38.4.4.1 Synthesis of Product Subclass 4 161
38.4.4.1.1 Method 1: Synthesis of Magnesium Alkyl Peroxides 161
38.4.4.1.1.1 Variation 1: Reaction of Organomagnesium Halides
with Oxygen 161
38.4.4.1.2 Method 2: Synthesis of Strontium Alkyl Peroxides 162
38.4.4.1.3 Method 3: Synthesis of Barium Alkyl Peroxides 162
38.4.5 Product Subclass 5: Group 1 Salts of Alkyl Hydroperoxides 162
38.4.5.1 Synthesis of Product Subclass 5 162
38.4.5.1.1 Method 1: Synthesis of Lithium Alkyl Peroxides 163
38.4.5.1.2 Method2: Synthesis of Sodium Alkyl Peroxides 163
38.4.5.1.2.1 Variation 1: Reaction of Sodium tert-Butoxide with
Alkyl Hydroperoxides 163
38.4.5.1.3 Method 3: Synthesis of Potassium Alkyl Peroxides 163
38.4.6 Product Subclass 6: Transition Metal Salts of Alkyl Hydroperoxides 164
38.4.6.1 Synthesis of Product Subclass 6 164
38.4.6.1.1 Method 1: Synthesis of Zinc Alkyl Peroxides 164
38.4.6.1.2 Method 2: Synthesis of Cadmium Alkyl Peroxides 164
38.4.6.1.2.1 Variation 1: Reaction ofAlkylcadmium(ll) Compounds with
Alkyl Hydroperoxides 165
38.4.6.1.3 Method3: Synthesis of Mercury Alkyl Peroxides 165
38.4.6.1.4 Method 4: Synthesis of Palladium Alkyl Peroxides 166
38.4.6.1.4.1 Variation 1: Reaction of Palladium(ll) Carboxylates with
Alkyl Hydroperoxides 166
38.4.6.1.4.2 Variation 2: Reaction of an Alkyl(bisphosphine)(hydroxy)palladium(ll)
Complex with an Alkyl Hydroperoxide 166
38.4.6.1.4.3 Variation 3: Reaction of (Dioxygen)bis(triphenylphosphine)palladium(ll)
with Electron-Deficient Alkenes 167
38.4.6.1.5 Method 5: Synthesis of Platinum Alkyl Peroxides 167
38.4.6.1.5.1 Variation 1: Reaction of Hydroxy(organo)bis(triorganophosphine)-
platinum(ll) Complexes with Alkyl Hydroperoxides 167
38.4.6.1.5.2 Variation 2: Reaction of (Dioxygen)bis(triphenylphosphine)platinum(ll)
Complexes with Electron-Deficient Alkenes 168
38.4.6.1.5.3 Variation 3: Reaction of (Dioxygen)bis(triphenylphosphine)platinum(ll)
Complexes with Carbonyl Compounds 169
38.4.6.1.6 Method 6: Synthesis of Cobalt Alkyl Peroxides 170
38.4.6.1.6.1 Variation 1: Reaction ofOrganocobaloximes with Oxygen 170
38.4.6.1.6.2 Variation 2: Reaction ofCobalt(ll) Complexes with
Alkyl Hydroperoxides 171
38.4.6.1.6.3 Variation 3: Reaction ofCobalt(ll) Complexes with
Oxygen and Phenols 171
38.4.6.1.6.4 Variation 4: Reaction of Cobalt(ll) Superoxo Complexes with
Phenoxyl Radicals 173
38.4.6.1.7 Method 7: Synthesis of Indium Alkyl Peroxide 173
38.4.6.1.8 Method 8: Synthesis of Titanium and Zirconium
Alkyl Peroxides 174
38.4.6.1.9 Method9: Synthesis of Molybdenum and Tungsten
Alkyl Peroxides 174
38.4.6.1.10 Method 10: Synthesis of Hafnium Alkyl Peroxides 175
38.4.6.1.H Method 11: Synthesis of Vanadium Alkyl Peroxides 176
38.5 Product Class 5: Alkyl and Cycloalkyl Peroxides
C. Vassilikogiannakis and T. Montagnon
38.5 Product Class 5: Alkyl and Cycloalkyl Peroxides 179
38.5.1 Synthesis of Product Class 5 180
38.5.1.1 Method 1: Nucleophilic Substitution 180
38.5.1.1.1 Variation 1: Reaction of Alkyl Hydroperoxides with Alkyl Bromides or
Methanesulfonates under Basic Conditions 180
38.5.1.1.2 Variation 2: Reaction of Alkyl Bromides orSulfonates
with Potassium Superoxide 182
38.5.1.1.3 Variation 3: Phase-Transfer-Catalyzed Synthesis of Primary-Tertiary
Bisperoxides 183
38.5.1.1.4 Variation 4: Reaction between Germanium or Tin Peroxides
and Alkyl Trifluoromethanesulfonates 184
38.5.1.1.5 Variation 5: Acid-Catalyzed Reaction of Alkyl Hydroperoxides
with Tertiary Alkyl Trichloroacetimidates 185
38.5.1.1.6 Variation 6: Reaction of Alkyl Hydroperoxides with Alkyl Bromides
in Ionic Liquids 187
38.5.1.1.7 Variation7: 1,1-Bis(alkylperoxy)alkanesviaAlkylationof
1,1-Bis(hydroperoxy)alkanes 187
38.5.1.2 Method 2: Addition to a Double Bond 190
38.5.1.2.1 Variation 1: Acid-Catalyzed Addition of Alkyl Hydroperoxides to
Enol Ethers 190
38.5.1.2.2 Variation 2: Base-Catalyzed Addition of Alkyl Hydroperoxides to
Electron-Deficient Alkenes 191
38.5.1.2.3 Variation 3: Peroxymercuration of Alkenes Followed by
Bromodemercuration 192
38.5.1.2.4 Variation 4: Cobalt-Catalyzed Triethylsilylperoxidation of
Alkenes with Molecular Oxygen 193
38.5.1.3 Method 3: Peroxycarbenium-Mediated C—C Bond Formation
from Monoperoxyketals and Monoperoxyacetals 194
38.5.1.3.1 Variation 1: Allylation of Monoperoxyketals and Monoperoxyacetals ••• 196
38.5.1.3.2 Variation2: Crotylation of Monoperoxyacetals 197
38.5.1.3.3 Variation 3: Synthesis of 3-Peroxy Ketones 198
38.5.1.3.4 Variation 4: Synthesis of 3-Peroxy Esters 199
38.5.1.4 Method 4: Opening of Oxetanes with Alkyl Hydroperoxides 199
38.5.1.5 Method 5: Opening of Epoxides with Alkyl Hydroperoxides 200
38.5.1.6 Method 6: Ruthenium-Catalyzed Oxidation of Tertiary Amines
with Alkyl Hydroperoxides 201
38.5.1.7 Method 7: Epoxy Alkyl Peroxides from Allylic Alcohols Bearing
an Appropriately Positioned Lactam Ring 202
38.6 Product Class 6: Allylic Peroxides
I. N. Lykakis and M. Stratakis
38.6 Product Class 6: Allylic Peroxides 205
38.6.1 Synthesis of Product Class 6 205
38.6.1.1 Method 1: Nudeophilic Substitution 205
38.6.1.1.1 Variation 1: Reaction of Allylic Bromides with Alkyl Hydroperoxides
under Basic Conditions 205
38.6.1.1.2 Variation 2: Alkylation of Hydroperoxyacetals under
Basic Conditions 206
38.6.1.1.3 Variation 3: Diallylation of 1,1-Bis(hydroperoxy)alkanes under
Basic Conditions 207
38.6.1.1.4 Variation 4: Alkylation of Allylic Hydroperoxides with an Alkyl Halide or
Sulfonate under Basic Conditions 208
38.6.1.1.5 Variation 5: Reaction of Allylic Alcohols with tert-Butyl Hydroperoxide
under Acidic Conditions 208
38.6.1.1.6 Variation 6: Reaction ofAllylic Alcohols with tert-Butyl Hydroperoxide
Catalyzed by a Polyoxometalate 209
38.6.1.1.7 Variation 7: Reaction of Alkyl Hydroperoxides and Tertiary Alkyl
Trichloroacetimidates under Acidic Conditions 210
38.6.1.2 Method 2: Synthesis ofAllylic Peroxides via Tritylation and
Methoxymethylation ofAllylic Stannyl Peroxides 211
38.6.1.3 Method 3: Allylic Peroxyketals via the Acid-Catalyzed Addition
ofAllylic Hydroperoxides to Enol Ethers 212
38.6.1.4 Method 4: Allylic Peroxidation of Alkenes with
tert-Butyl Hydroperoxide 213
38.6.1.4.1 Variation 1: Palladium-Catalyzed Allylic Peroxidation
ofCydoalkenes 213
38.6.1.4.2 Variation 2: Palladium/Carbon-Catalyzed Allylic Peroxidation
of1,4-Dienes 214
38.6.1.4.3 Variation 3: Palladium(ll) Hydroxide/Carbon Catalyzed Allylic
Peroxidation of Enones 215
38.6.1.4.4 Variation 4: Allylic Peroxidation of Cyclohexene Catalyzed by
Manganese(ll), Cobalt(ll), Nickel(ll), Copper(ll), and
Vanadyl Complexes Supported on Alumina 215
38.6.1.4.5 Variation 5: Allylic Peroxidation of Cyclohexene Catalyzed by Molybdenum
Oxide and Vanadium Oxide Clusters 217
38.6.1.4.6 Variation 6: Allylic Peroxidation of Cycloalkenes with tert-Butyl
Hydroperoxide Catalyzed by Pyridinium Chlorochromate
orPyridiniumDichromate 218
38.6.1.5 Method 5: Reaction of Conjugated Dienes and Trienes with Pyridinium
Dichromate and tert-Butyl Hydroperoxide 218
38.6.1.6 Method 6: Hexacarbonylmolybdenum(0)-Catalyzed Oxidation
of Enediones with tert-Butyl Hydroperoxide To
Form Peroxypyranones 219
38.6.1.7 Method 7: Synthesis of Functionalized Allylic Peroxides from
Allylic PeroxyVinylstannanes 220
38.6.1.7.1 Variation 1: N-lodosuccinimide-Mediated Formation ofAllylic
Peroxy Vinyl Iodides ¦•¦ 221
38.6.1.7.2 Variation 2: Palladium-Mediated C—C Bond-Forming Reactions for the
Synthesis of Functionalized Allylic Peroxides 221
38.6.1.8 Method 8: Synthesis of Allylic Peroxides via the Wittig Alkenation of
a-Peroxy-Substituted Aldehydes 223
38.6.1.9 Method 9: Formation of 4-(tat-Butylperoxy)cydohexadienones by
Oxidation of Phenols 224
38.6.1.9.1 Variation 1: Metal-Catalyzed Oxidation of Phenols with
tert-Butyl Hydroperoxide 224
38.6.1.9.2 Variation 2: Free-Radical Oxidation of Phenols by a
Hypervalent (tert-Butylperoxy)iodane and
tert-Butyl Hydroperoxide 226
38.6.1.10 Method 10: Formation of Allylic 1,4-Diperoxides from the
Chloroperoxidase-Catalyzed Oxidation of
Conjugated Dienoic Esters 226
38.7 Product Class 7: Benzylic Peroxides
M. R. lesce and M. DellaGreca
38.7 Product Class 7: Benzylic Peroxides 231
38.7.1 Synthesis of Product Class 7 231
38.7.1.1 Oxidation with Oxygen 231
38.7.1.1.1 Method 1: Oxidation of Arylalkanes 231
38.7.1.1.2 Method 2: Oxidation of Triarylmethyl Chlorides 232
38.7.1.1.3 Method3: Oxidation of Arylalkenesvia Trapping Reactions 232
38.7.1.1.3.1 Variation 1: Intramolecular Cyclization in the Presence of a
Cobalt(ll) Complex 232
38.7.1.1.3.2 Variation 2: IntermolecularCycloadditionwithCarbonyl Compounds ••• 233
38.7.1.1.3.3 Variation 3: Intermolecular Cyclization with p"-Oxo Carbonyl Compounds
in the Presence of Manganese Catalysts 234
38.7.1.1.3.4 Variation 4: Intermolecular Cyclization with Heterocyclic 1,3-Dicarbonyl
Compounds in the Presence of Manganese Catalysts 236
38.7.1.2 Oxidation with Hydroperoxides 238
38.7.1.2.1 Method 1: Oxidation of Arylalkanes under Metal Catalysis 238
38.7.1.2.1.1 Variation 1: Using Chromium 238
38.7.1.2.1.2 Variation 2: Using Cobalt 239
38.7.1.2.1.3 Variation 3: Using Copper 240
38.7.1.2.1.4 Variation 4: Using Lead 243
38.7.1.2.2 Method 2: Nucleophilic Substitution Using Hydroperoxides 244
38.7.1.2.2.1 Variations OfHalides 244
38.7.1.2.2.2 Variation 2: Of Alcohols 247
38.7.1.2.2.3 Variation 3: Oflmidates 249
38.7.1.2.2.4 Variation 4: OfOxiranes 249
38.7.1.2.3 Method 3: Addition Reactions of Hydroperoxides 250
38.7.1.2.3.1 Variation 1: Acid-Mediated Addition to Alkenes 250
38.7.1.2.3.2 Variation 2: Base-Mediated Addition to Alkenes 251
38.7.1.2.3.3 Variation 3: Palladium-Mediated Addition to Alkenes 252
38.7.1.2.3.4 Variation 4: Mercury-Mediated Addition to Alkenes 253
38.7.1.2.3.5 Variation 5: Addition to Cyclopropanes 254
38.7.1.2.3.6 Variation 6: Addition to Carbonyl Compounds 256
38.7.1.3 Photooxygenation 257
38.7.1.3.1 Method 1: Photooxygenation of Arylalkenes 257
38.7.1.3.2 Method 2: Photooxygenation of Three-Membered Heterocycles via
Photoinduced Electron Transfer 258
38.7.1.3.3 Method 3: Photooxygenation of Cyclopropanes via Photoinduced
Radical Production 260
38.7.1.4 OtherMethods 260
38.7.1.4.1 Method 1: Oxidative Fluorodesulfuration 260
38.7.1.4.2 Method 2: OzonizationofUnsaturatedBenzylicHydroperoxides 261
38.7.1.4.3 Method 3: Oxygenation of Aryl Azo Hydroperoxides 262
38.7.1.4.4 Method 4: Acid-Catalyzed Reaction of Peroxyketals with
KeteneSilylAcetals 262
38.7.2 Applications of Product Class 7 in Organic Synthesis 264
38.7.2.1 Method 1: Oxidation to Carbonyl Derivatives 264
38.7.2.2 Method2: Reduction to Alcohols 265
38.7.2.3 Method 3: HeterolysisofanO-OorC-OBond 265
38.7.2.3.1 Variation 1: Trapping with Alkenes 267
38.7.2.3.2 Variation 2: Trapping with Carbonyl Compounds 268
38.7.2.3.3 Variation 3: Trapping with Hydrazine Derivatives or Hydroxylamine 269
38.7.2.4 Method 4: HomolysisoftheO-0 Bond: Radical Production 270
38.8 Product Class 8: Monocyclic Peroxides
38.8.1 Product Subclass 1: Three-Membered Cyclic Peroxides (Dioxiranes)
B.Wang and Y.Shi
38.8.1 Product Subclass 1: Three-Membered Cyclic Peroxides (Dioxiranes) 275
38.8.1.1 Synthesis of Product Subclass 1 275
38.8.1.1.1 Method 1: Preparation of Dioxiranes Using Oxone 276
38.8.1.2 Applications of Product Subclass 1 in Organic Synthesis 278
38.8.1.2.1 Method 1: Oxidation of Heteroatoms by Dioxiranes 278
38.8.1.2.1.1 Variation 1: Synthesis of Sulfinic Acids 279
38.8.1.2.1.2 Variation 2: Synthesis of Sulfoxides and Sulfones 279
38.8.1.2.1.3 Variation 3: Synthesis of Sulfoximides 283
38.8.1.2.1.4 Variation 4: Synthesis of/V-Oxides and Nitro Compounds 283
38.8.1.2.1.5 Variation5: Synthesis of Hydroxylamines 287
38.8.1.2.1.6 Variation 6: Synthesis ofNitrones and Nitroxide Radicals 289
38.8.1.2.1.7 Variation 7: Synthesis of Hydroxamic Acids 292
38.8.1.2.1.8 Variation 8: Cleavage of C=N Bonds 293
38A1.2.1.9 Variation 9: Cleavage of C=P Bonds 297
38.8.1.2.1.10 Variation 10: Cleavage of C=S Bonds 298
38.8.1.2.2 Method 2: Oxidation of C=C it-Bonds by Dioxiranes 300
38.8.1.2.2.1 Variation 1: Oxidation of Alkenes 300
38.8.1.2.2.2 Variation 2: Oxidation of Allenes 300
38.8.1.2.2.3 Variation 3: Oxidation of Enolates 303
38.8.1.2.2.4 Variation 4: Oxidation of Arenes 306
38.8.1.2.2.5 Variation 5: Oxidation of Alkynes 310
38.8.1.2.3 Method 3: Oxidation ofX—Ho-Bonds by Dioxiranes 310
38.8.1.2.3.1 Variation 1: Oxidation of Si—Ha-Bonds 310
38.8.1.2.3.2 Variation 2: Oxidation C—Ho-Bonds of Saturated Alkanes 311
38.8.1.2.3.3 Variation 3: Oxidation of Activated C—Ha-Bonds 314
38.8.1.2.4 Method 4: Oxidation of Organometallic Compounds by Dioxiranes — 316
38.8.2 Product Subclass 2: Four-Membered Cyclic Peroxides
(1,2-Dioxetanes and 1,2-Dioxetanones)
W. J. Baader and E. L. Bastos
38.8.2 Product Subclass 2: Four-Membered Cyclic Peroxides
(1,2-Dioxetanes and 1,2-Dioxetanones) 323
38.8.2.1 Synthesis of Product Subclass 2 324
38.8.2.1.1 Method 1: Cyclization of Halo Hydroperoxides 324
38.8.2.1.1.1 Variation 1: Cyclization of Epoxy Hydroperoxides 326
38.8.2.1.1.2 Variation 2: Cyclization of Unsaturated Hydroperoxides 326
38.8.2.1.1.3 Variation 3: By Cyclomercuration ofAllylic Hydroperoxides 328
38.8.2.1.1.4 Variation 4: 1,2-Dioxetanonesfroma-HydroperoxyAcids 328
38.8.2.1.2 Method 2: Singlet Oxygenation of Alkenes 329
38.8.2.1.2.1 Variation 1: By Sensitized Photooxygenation 330
38.8.2.1.2.2 Variation 2: Using Calcium Peroxide-Hydrogen Peroxide Complex 333
38.8.2.1.2.3 Variation 3: Using Sodium Molybdate/Hydrogen Peroxide 334
38.8.2.1.2.4 Variation 4: Using Triethylsilyl Hydrotrioxide 335
38.8.2.1.3 Method 3: Triplet Oxygenation of Cyclobutadienes 335
38.8.2.1.4 Method 4: Photocatalytic Oxygenation 336
38.8.2.1.5 Method 5: OzonolysisofVinylsilanes 337
38.8.2.1.6 Method 6: Oxygenation Using Phosphite Ozonides 338
38.8.2.1.6.1 Variation 1: 1,2-Dioxetanones from Photooxygenation of Ketenes 340
38.8.2.1.7 Method 7: Electron-Transfer Oxygenation 340
38.8.3 Product Subclass 3: Five-Membered Cyclic Peroxides with No Further
Heteroatoms in the Ring (1,2-Dioxolanes and 1,2-Dioxolan-3-ones)
W. j. Baader and E. L. Bastos
38.8.3 Product Subclass 3: Five-Membered Cyclic Peroxides with No Further
Heteroatoms in the Ring (1,2-Dioxolanes and 1,2-Dioxolan-3-ones) 345
38.8.3.1 Synthesis of Product Subclass 3 346
38.8.3.1.1 Method 1: Cyclization of Hydroperoxides 346
38.8.3.1.1.1 Variation 1: OfBromoHydroperoxides 346
38.8.3.1.1.2 Variation 2: Of Epoxy Hydroperoxides 347
38.8.3.1.1.3 Variation 3: Of Vinyl Hydroperoxides 347
38.8.3.1.1.4 Variation 4: Of Stannylalkenyl Hydroperoxides 349
38.8.3.1.1.5 Variation 5: Ofa-Alkoxy Hydroperoxides 350
38.8.3.1.1.6 Variation 6: Lead(IV) Acetate Mediated Cydization of
3-Phenylpropyl Hydroperoxides 350
38.8.3.1.2 Method 2: Cydization of Haloalkyl Peroxides ¦ 351
38.8.3.1.3 Method 3: Cydization of Oxetane Hydroperoxyacetals 351
38.8.3.1.4 Method 4: Oxidation of a,|3-Unsaturated Ketones by
Hydrogen Peroxide 353
38.8.3.1.5 Method 5: Peroxymercuration/Demercuration 355
38.8.3.1.6 Method6: Cydoaddition of Carbonyl Oxides to C—C Multiple Bonds ¦¦¦ 356
38.8.3.1.6.1 Variation 1: From 1,2,4-Trioxolanes 356
38.8.3.1.6.2 Variation 2: Via Peroxycarbenium Ions 358
38.8.3.1.7 Method7: SingletOxygenation 359
38.8.3.1.7.1 Variation 1: Of 2-Methylacrylic Adds, Leading to 3-Hydroperoxy Adds •• 359
38.8.3.1.7.2 Variation2: OfEnones 360
38.8.3.1.7.3 Variation 3: OfCydopropanes 361
38.8.3.1.7.4 Variation 4: Ofa.p-UnsaturatedAldimines 362
38.8.3.1.8 Method 8: Radical-Mediated Oxygenation 362
38.8.3.1.8.1 Variation 1: Addition of Molecular Oxygen to Cydopropanes 362
38.8.3.1.8.2 Variation 2: From Stable Schlenk Hydrocarbon Diradicals 366
38.8.3.1.8.3 Variation 3: Peroxidation of 1,4-Dienes and Vinylcyclopropanes with
Cobalt(ll)/Oxygen/Triethylsilane 367
38.8.3.1.8.4 Variation 4: Photolysis or Thermolysis of Alkylidene Azoalkanes 368
38.8.3.1.8.5 Variation 5: Thiol-Alkene Co-oxygenation 369
38.8.3.1.8.6 Variation 6: Halogen-Mediated Peroxidations 370
38.8.3.1.9 Method 9: P-Fragmentation of Alkoxy Radicals 370
38.8.3.1.10 Method 10: Synthesis from Benzo-Fused Bicyclic Sulfonium Salts 372
38.8.3.1.11 Method 11: Ozonolysis 373
38.8.3.1.12 Method12: Peroxide Addition 375
38.8.4 Product Subclass 4: Five-Membered Cyclic Peroxides with One Further
Oxygen Atom in the Ring (1,2,4-Trioxolanes)
W. J. Baader and E. L. Bastos
38.8.4 Product Subclass 4: Five-Membered Cyclic Peroxides with One Further
Oxygen Atom in the Ring (1,2,4-Trioxolanes) 379
38.8.4.1 Synthesis of Product Subclass 4 380
38.8.4.1.1 Methodi: Ozonolysis of Alkenes 380
38.8.4.1.2 Method 2: Cydoaddition of Carbonyl Oxides to C=O Bonds 385
38.8.4.1.2.1 Variation 1: From the Ozonolysis of Cycloalkadienes in the
Presence of Carbonyl Compounds 387
38.8.4.1.2.2 Variation 2: GriesbaumCo-ozonolysis 387
38.8.4.1.3 Method 3: Ozonolysis of Acetylenic Substrates 389
38.8.4.1.4 Method 4: Photooxygenation 390
38.8.4.1.4.1 Variation 1: OfEpoxides 390
38.8.4.1.4.2 Variation 2: OfFurans 391
38.8.4.1.4.3 Variation 3: OfDiazo Compounds and Azines 392
38.8.5 Product Subclass 5: Six-Membered Cyclic Peroxides with No Further
Heteroatoms in the Ring (1,2-Dioxanes and 3,6-Dihydro-1,2-dioxins)
W. J. Baader and E. L. Bastos
38.8.5 Product Subclass 5: Six-Membered Cyclic Peroxides with No Further
Heteroatoms in the Ring (1,2-Dioxanes and 3,6-Dihydro-1,2-dioxins) • - - 397
38.8.5.1 Synthesis of Product Subclass 5 398
38.8.5.1.1 Method 1: Cyclization of Hydroperoxides 398
38*5.1.1.1 Variation 1: Cyclization of Halo Hydroperoxides 398
38.8.5.1.1.2 Variation 2: Cyclization of Epoxy Hydroperoxides 399
38.8.5.1.1.3 Variation 3: Cyclization of Vinyl Hydroperoxides 400
38.8.5.1.1.4 Variation 4: Cyclization of Oxetane Hydroperoxides 401
38.8.5.1.2 Method 2: Cyclization of Unsaturated Hydroperoxyacetals 402
38.8.5.1.3 Method 3: Cydoaddition of Carbonyl Oxides to C—C Multiple Bonds ••• 404
38.8.5.1.4 Method 4: OzonolysisofAlkylidenecydopropanes 406
38.8.5.1.5 Method 5: Singlet Oxygenation of 1,3-Dienes and
Related Compounds 407
38.8.5.1.6 Method 6: Radical-Mediated Oxygenation 409
38.8.5.1.6.1 Variation 1: Thiol-Alkene Co-oxygenation 409
38.8.5.1.6.2 Variation 2: Free-Radical Cyclization of Alkenes with
Carbonyl Compounds 409
38.8.5.1.6.3 Variation 3: Peroxyl-Radical Cyclization 411
38.8.5.1.6.4 Variation 4: Peroxidation with Cobalt(ll)/Oxygen/Triethylsilane 412
38.8.5.1.6.5 Variation 5: Oxygen Addition to Carbon-Centered Radicals 413
38.8.5.1.6.6 Variation 6: Lead(IV) Acetate Mediated Cyclization of
co-Phenyl Hydroperoxides 414
38.8.5.1.6.7 Variation 7: Addition of Molecular Oxygen to Alkenes 414
38.8.5.1.7 Method 7: Photoenolization and Oxygenation of
a,P-Unsaturated Ketones 415
38.8.5.1.8 Method 8: Nudeophilic Addition of Peroxides 417
38.8.6 Product Subclass 6: Six-Membered Cyclic Peroxides with One Further
Oxygen Atom in the Ring (1,2,4-Trioxanes)
W. J. Baader and E. L. Bastos
38.8.6 Product Subclass 6: Six-Membered Cyclic Peroxides with One Further
Oxygen Atom in the Ring (1,2,4-Trioxanes) 421
38.8.6.1 Synthesis of Product Subclass 6 422
38.8.6.1.1 Method 1: Synthesis from Hydroperoxides 422
38*6.1.1.1 Variation 1: Condensation of P-Hydroperoxy Alcohols with
Aldehydes or Ketones 422
38.8.6.1.1.2 Variation 2: Cyclization of Unsaturated Hydroperoxyacetals 427
38.8.6.1.1.3 Variation 3: Autoxidation of Unsaturated Hydroperoxyacetals 430
38.8.6.1.1.4 Variation 4: From Epoxy Hydroperoxides 431
38.8.6.1.2 Method 2: Cyclization of Allylic Peroxyhemiketals 431
38.8.6.1.2.1 Variation 1: Mercury(ll)-Mediated Cyclization of
Unsaturated Peroxyhemiketals 432
38.8.6.1.3 Method 3: Cyclization of Silyl Peroxyhemiketals in the Presence of
Aldehydes and Ketones 433
38.8.6.1.3.1 Variation 1: 1,2,4-Trioxan-5-ones from a-(Trimethylsilylperoxy) Esters •¦ 433
38.8.6.1.4 Method 4: Photooxygenation 434
38.8.6.1.5 Method 5: Synthesis from 1,2-Dioxetanes: The Posner Reaction 435
38.8.6.1.6 Method 6: Miscellaneous Methods Employing Bridged
Cyclic Peroxides 439
38.8.6.1.7 Method 7: Addition of Oxygen to Allylic Hydroperoxides 441
38.8.6.1.8 Method 8: Trapping of Paterno-Buchi1,4-Diradicals by
Molecular Oxygen 444
38.8.6.1.9 Method 9: Autoxidation of Imines in the Presence of Aldehydes 445
38.8.7 Product Subclass 7: Six-Membered Cyclic Peroxides with Two Further
Oxygen Atoms in the Ring (1,2,4,5-Tetroxanes)
W. J. Baaderand E. L Bastos
38.8.7 Product Subclass 7: Six-Membered Cyclic Peroxides with Two Further
Oxygen Atoms in the Ring (1,2,4,5-Tetroxanes) 449
38.8.7.1 Synthesis of Product Subclass 7 450
38.8.7.1.1 Method 1: Synthesis from Aldehydes or Ketones 450
38.8.7.1.1.1 Variation 1: Reaction of Aldehydes or Ketones with
Bis(trimethylsilyl) Peroxide 456
38.8.7.1.2 Method 2: Synthesis by Ozonolysis 458
38.8.7.1.2.1 Variation 1: OfO-Methyloximes 461
38.8.7.1.3 Method 3: Synthesis from 1,2,4-Trioxolanes 462
38.8.7.1.4 Methods 4: Miscellaneous Methods 463
38.9 Product Class 9: Larger-Ring Cyclic Peroxides and Endoperoxides
M. N. Alberti, M. D. Tzirakis, and M. Orfanopoulos
38.9 Product Class 9: Larger-Ring Cyclic Peroxides and Endoperoxides 469
38.9.1 Synthesis of Product Class 9 469
38.9.1.1 Method 1: Peroxidation with Triplet Molecular Oxygen 469
38.9.1.1.1 Variation 1: CycloadditionofTripletDioxygentoBiradicals 469
38.9.1.1.2 Variation 2: Cycloaddition of Triplet Oxygen to an
o-Quinodimethane System 470
38.9.1.1.3 Variation 3: Electron-Transfer-Induced Photooxidation of 1,6-Dienes
with Triplet Oxygen 471
38.9.1.1.4 Variation 4: Lewis Acid Induced Peroxidation of 1,3-Dienes 473
38.9.1.1.5 Variation 5: Autoxidation of Nonconjugated 1,4-Dienes 474
38.9.1.1.6 Variation 6: Thiol-Alkene Co-oxygenation 475
38.9.1.1.7 Variation 7: Coba!t(ll)-Catalyzed Peroxidation of 1,5-Dieneswith
Molecular Oxygen and Triethylsilane 478
38.9.1.2 Method 2: Oxidation of Cyclic Unsaturated Compounds with
Photochemically Generated Singlet Oxygen 479
38.9.1.2.1 Variation 1: Photooxidation of Naphthalene Derivatives 480
38.9.1.2.2 Variation 2: Photooxidation of Anthracene and Pentacene Derivatives 483
38.9.1.2.3 Variation 3: Photooxidation of Strained Metacyclophanes 485
38.9.1.2.4 Variation 4: Photooxidation of Cyclopentadiene and Cyclohexa-1,3- or
Cyclohexa-1,4-diene Systems 485
38.9.1.2.5 Variation 5: Photooxidation of Cycloheptadiene/triene Systems 488
38.9.1.2.6 Variation 6: Photooxidation of Cyclooctadiene/triene/tetraene Systems 492
38.9.1.3 Method 3: Oxidation of Cyclic Unsaturated Compounds by Chemically
Generated Singlet Oxygen 493
38.9.1.4 Method 4: Cyclization of Hydroperoxides and Their Derivatives through
Nucleophilic Substitution 494
38.9.1.4.1 Variation 1: Cyclization of Bromo Hydroperoxides 494
38.9.1.4.2 Variation 2: Acid-Catalyzed Cyclization of Epoxy Hydroperoxides 496
38.9.1.4.3 Variation 3: Trimethylsilyl Trifiuoromethanesulfonate Catalyzed
Intramolecular Cyclization of Silyl Peroxides 496
38.9.1.4.4 Variation4: Peroxide Transfer from Bis(tributyltin) Peroxide 497
38.9.1.4.5 Variation 5: Cesium Hydroxide orSilver(l) Oxide Mediated Cydoalkylation
ofAlkane-1,1-diylDihydroperoxidesandDihaloalkanes — 498
38.9.1.4.6 Variation 6: Base-Catalyzed Cyclization of Dihydroperoxides
and Dialkyldichlorosilanes 499
38.9.1.5 Method 5: Cyclization of Unsaturated Hydroperoxides through
Intramolecular N ucleophilic Addition 500
38.9.1.5.1 Variation 1: Halonium Ion Mediated Cyclization of
Unsaturated Hydroperoxides 500
38.9.1.5.2 Variation 2: Base-Catalyzed Intramolecular Cyclization of
Unsaturated Hydroperoxides 504
38.9.1.5.3 Variation 3: Ozonolysis of Unsaturated Hydroperoxides 505
38.9.1.5.4 Variation 4: Ozonolysis of Vinylsilanes 508
38.9.1.5.5 Variation 5: Peroxymercuration/Demercuration of Cyclic Dienes 509
38.9.1.5.6 Variation6: Intramolecular Capture of P-Hydroperoxy Cations 510
38.9.1.6 Method 6: Cycloaddition of Peroxides with Carbonyl Compounds 511
38.9.1.6.1 Variation 1: Trimethylsilylation of Dihydroperoxides Followed by
Trimethylsilyl Trifiuoromethanesulfonate Catalyzed
Cyclocondensation with Carbonyl Compounds 511
38.9.1.6.2 Variation 2: Acid-Catalyzed Condensation of y- or 6-Hydroxy
Hydroperoxides and Ketones 512
38.9.1.6.3 Variation 3: Acid-Catalyzed Condensation of 3-Methyl-3-
(triethylsilylperoxy)butan-i -ol and Carbonyl Compounds • • • 514
38.9.1.7 Method 7: Synthesis with Retention of the Functional Group 515
38.9.1.7.1 Variation 1: Reduction ofC=C Bonds in Unsaturated Bicyclic Peroxides •¦ 515
38.9.1.7.2 Variation 2: Chlorination of Unsaturated Bicyclic Peroxides 517
38.9.1.7.3 Variation 3: Selective Reduction of the Hydroperoxide Group in
Hydroperoxy Endoperoxides 517
38.9.1.7.4 Variation 4: Dehydration of Hydroperoxy-Substituted Endoperoxides ••• 517
38.9.1.7.5 Variation 5: Reduction of a Ketone Group in Endoperoxides 519
38.9.1.7.6 Variation 6: Oxidation of Hydroxy Endoperoxides 519
38.9.1.7.7 Variation 7: Diels-Alder Reaction with Dimethyl 1,2,4,5-Tetrazine-3,6-
dicarboxylate 520
38.9.1.7.8 Variation 8: Reductive Debromination with Tributyltin Hydride 520
38.9.1.7.9 Variation 9: Silver(l) Oxide Mediated Methylation of Hydroperoxy-
Substituted Endoperoxides 521
Keyword Index 525
Author Index 555
Abbreviations 577 |
| any_adam_object | 1 |
| author | Berkessel, Albrecht |
| author2 | Alberti, M. N. |
| author2_role | edt |
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| author_GND | (DE-588)1206253118 (DE-588)117013870 |
| author_facet | Berkessel, Albrecht Alberti, M. N. |
| author_role | aut |
| author_sort | Berkessel, Albrecht |
| author_variant | a b ab |
| building | Verbundindex |
| bvnumber | BV035240516 |
| ctrlnum | (OCoLC)634589059 (DE-599)BVBBV035240516 |
| format | Book |
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| id | DE-604.BV035240516 |
| illustrated | Illustrated |
| indexdate | 2024-08-20T00:15:10Z |
| institution | BVB |
| isbn | 9783131189110 9781588905291 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-017046319 |
| oclc_num | 634589059 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-210 DE-91G DE-BY-TUM DE-11 |
| owner_facet | DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-210 DE-91G DE-BY-TUM DE-11 |
| physical | XXV, 582 Seiten Illustrationen 26 cm |
| publishDate | 2009 |
| publishDateSearch | 2009 |
| publishDateSort | 2009 |
| publisher | Thieme |
| record_format | marc |
| spelling | Berkessel, Albrecht Verfasser (DE-588)1206253118 aut Science of synthesis Houben-Weyl methods of molecular transformations 38 = Category 5, Compounds with one saturated carbon-heteroatom bond Peroxides ed. board: D. Bellus ... Stuttgart [u.a.] Thieme 2009 XXV, 582 Seiten Illustrationen 26 cm txt rdacontent n rdamedia nc rdacarrier Bellus, Daniel Sonstige oth Alberti, M. N. edt Houben, Josef 1875-1940 Sonstige (DE-588)117013870 oth (DE-604)BV013247070 38 Erscheint auch als Online-Ausgabe 978-3-13-183931-2 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017046319&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Science of synthesis Houben-Weyl methods of molecular transformations Berkessel, Albrecht |
| 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_full | Science of synthesis Houben-Weyl methods of molecular transformations 38 = Category 5, Compounds with one saturated carbon-heteroatom bond Peroxides ed. board: D. Bellus ... |
| title_fullStr | Science of synthesis Houben-Weyl methods of molecular transformations 38 = Category 5, Compounds with one saturated carbon-heteroatom bond Peroxides ed. board: D. Bellus ... |
| title_full_unstemmed | Science of synthesis Houben-Weyl methods of molecular transformations 38 = Category 5, Compounds with one saturated carbon-heteroatom bond Peroxides ed. board: D. Bellus ... |
| title_short | Science of synthesis |
| title_sort | science of synthesis houben weyl methods of molecular transformations peroxides |
| title_sub | Houben-Weyl methods of molecular transformations |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017046319&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV013247070 |
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