Synthesis of aromatic compounds:
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Berlin ; Boston
De Gruyter
[2022]
|
| Schriftenreihe: | De Gruyter STEM
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XV, 372 Seiten Illustrationen |
| ISBN: | 9783110562675 |
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| 300 | |a XV, 372 Seiten |b Illustrationen | ||
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| 650 | 4 | |a Organische Synthese | |
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Datensatz im Suchindex
| _version_ | 1804184382401937408 |
|---|---|
| adam_text | Contents
Preface —V
List of abbreviations —— Xill
Introduction — aromatic compounds and aromaticity —1
Importance of aromatic compounds ——1
Synthetic dyes —1
Biologically active compounds ——-3
Aromatic compounds in materials science — 4
Aromaticity — 5
Stability of aromatic compounds — 6
Structure and reactivity of aromatic compounds — 8
Magnetic properties of aromatic compounds — 8
In this book — 10
References — 11
Electrophilic aromatic substitution — 13
Introduction — 13
General mechanistic principles — 13
Scope of electrophilic aromatic substitution — 13
Nitration — 14
Sulfonation — 15
Halogenation — 16
Carbon electrophiles: Friedel-Crafts alkylation and acylation — 17
Substituent effects in electrophilic aromatic substitution — 20
Reactivity — 20
Regioselectivity of electrophilic substitution of aromatic
compounds — 21
Regioselectivity in polysubstituted benzenes — 23
Functional group interconversion to control reactivity and
regioselectivity — 26
Reduction of nitro groups —— 26
Reduction of acyl groups —— 27
Reactions at benzylic positions — 28
Acylation of phenols and anilines —— 29
Reversibility of etectrophilic aromatic substitution —— 30
Protiodesilylation — 31
Halodesilylation — 31
Electrophilic rearrangement — the Fries rearrangement —— 32
2 8
Electrophilic aromatic substitution of polycyclic aromatic
compounds — 33
Electrophilic aromatic substitution of heteroaromatic
compounds — 34
Five-membered heterocycles — 34
Six-membered heterocycles — 36
Further reading — 36
References — 36
Nucleophilic aromatic substitution reactions — 39
introduction —— 39
Addition-elimination of nucleophiles (SyAr) —— 39
Leaving groups in SyAr — 41
Regioselectivity in SyAr reactions —— 41
Examples of the utility of SyAr reactions — 43
Carbon nucleophiles in nucleophilic aromatic substitution —— 45
Reversibility of SyAr reactions — 47
The Smiles rearrangement: an intramolecular SyAr reaction — 48
Substitution via benzyne formation — 51
Concerted nucleophilic aromatic substitutions — 52
Nucleophilic substitution of heteroaromatic systems — 55
Substitution of aryl diazonium salts — 58
Diazonium salt formation — 58
Reactions of diazonium salts with nucleophilic species — 58
Other reactions of aryl diazonium salts — 63
Formation of biaryls: the Gomberg-Bachmann reaction
and Pschorr cyclization — 65
References — 67
Reactions of aryllithium species — 73
Introduction —— 73
Deprotonation of arenes: directed ortho metalation —— 74
Introduction to directed ortho metalation —— 74
Examples of directed ortho metalation in synthesis —— 77
Anionic ortho-Fries rearrangement — 79
Directed remote metalation —— 8 amp;2
Lithium-halogen exchange — 85
Rearrangements of haloarenes: halogen dance reactions — 86
References — 92
5 Benzynes —— 95
5 1 Introduction to benzynes —— 95
5 2 Formation of benzynes — 95
521 Aryne formation by elimination of H-X — 96
522 Aryne formation from dihalobenzenes — 100
523 Aryne formation by elimination of small molecules — 101
524 Fluoride-induced aryne formation — 102
5 3 Reactions of arynes — 105
531 Cycloaddition reactions — 106
5 3 11 [4 + 2] Cycloaddition reactions — 106
5312 Intramolecular Diels-Alder reactions — 108
5313 [2+2] Cycloadditions — 109
5314 1,3-Dipolar cycloadditions — 111
532 Reactions of arynes with nucleophiles —— 113
5321 Nucleophilic addition reactions — 113
5322 Multicomponent reactions of arynes — 115
5323 Aryne insertion reactions — 116
533 Transition metal-mediated reactions of arynes — 121
5 4 Meta- and para-didehydrobenzenes (m- and p-arynes) — 125
References — 126
6 Transition-metal-mediated C-C bond forming reactions of aromatic
compounds — 131
6 1 Introduction — 131
6 2 Preparation of biaryls via homocoupling — 132
621 Copper-mediated coupling: the Ullmann reaction — 132
622 Nickel-mediated homocoupling reactions — 135
623 Oxidative coupling reactions — 138
6 3 Preparation of biaryls via cross-coupling reactions — 139
631 Metal-catalyzed cross-coupling — 139
6311 Ar-X cross-coupling precursors — 142
6312 Suzuki-Miyaura cross-coupling (aryl boronic acids or boronate
esters) — 143
6313 Negishi cross-coupling (organozinc) — 145
6314 Stille cross-coupling (organotin) — 146
6315 The Hiyama cross-coupling (organosilanes) — 148
6316 Kumada-Corriu cross-coupling (Grignard reagents) — 149
6 4 Other coupling reactions — 150
641 The Heck reaction — 150
642 The Sonogashira reaction — 153
643 Transition metal-mediated cyanation — 159
6 5 Direct arylation (C-H functionalization) — 160
6 5 1
Introduction to direct arylation — 160
Direct arylation with aryl halides — 161
Intramolecular direct arylation reactions with aryl halides — 162
Direct arylation using directing groups — 163
Direct arylation without directing groups — 166
Direct arylation of heteroaromatic compounds — 167
Direct arylation using organometallic species — 170
Direct arylation with arenes: dehydrogenative coupling — 171
Axially chiral biaryls: synthetic approaches — 174
Atropisomerism and axial chirality — 174
Approaches to racemic atropisomeric biaryls — 176
Stereoselective approaches to axially chiral biaryls — 177
References — 182
Other transition-metal-mediated reactions of aromatic
compounds — 191
Introduction — 191
Aromatic C-N and C-O bond formation — 191
Copper-catalyzed aryl C-N and C-O bond formation — 191
Palladium-catalyzed aryl amination — 195
Transition-metal-catalyzed borylation reactions — 200
Palladium-catalyzed borylation of aryl halides — 201
lridium-catalyzed direct borylation — 204
References — 211
Constructing aromatic rings — 215
Introduction — 215
Preparing benzene rings from non-aromatic precursors — 215
Cycloaddition reactions — 215
Transition metal-catalyzed alkyne cyclotrimerization — 218
Olefin metathesis — 224
Preparing aromatic heterocycles — 226
Five-membered ring heterocycles —- 227
Six-membered ring heterocycles — 230
Fused heteroaromatics — 234
Synthesis of indoles — 234
Synthesis of quinolines —— 239
Synthesis of isoquinolines — 242
References — 244
9
Fused aromatic rings — polycyclic aromatic hydrocarbons — 247
Introduction to polycyctic aromatic hydrocarbons —— 247
Classification and nomenclature of PAHs —— 247
Stability and reactivity of PAHs —— 250
The aromatic sextet —— 250
General reactivity of PAHs —— 253
Synthetic approaches to PAHs —— 256
Haworth synthesis — 256
The Pschorr synthesis —— 260
The Elbs reaction — 260
Diels-Alder cycloadditions — 261
The Wittig reaction — 266
Photocyclization (the Mallory-Katz reaction) — 267
Cyclodehydrogenation reactions — 268
Cyclodehydrohalogenation reactions — 275
Aryne cyclotrimerization and related reactions — 276
Ring-closing metathesis — 277
Alkyne benzannulation — 279
Asao-Yamamoto benzannualation — 282
References — 284
Synthesis of select classes of polycyclic aromatic hydrocarbons — 289
Introduction — 289
Synthesis of linear fused aromatic structures - the acenes — 289
Synthetic approaches to pentacenes — 290
Synthesis of larger acenes — 293
Synthesis of phenacenes — 295
Perylenes and rylenes — 299
Synthesis of triphenylenes and related compounds — 301
Triphenylenes — 301
Trinaphthylenes and larger starphenes — 306
From coronenes to larger PAHs — 311
Graphene nanoribbons — 317
References — 324
Nonplanar aromatic compounds — 329
Introduction — 329
Helicenes and related contorted polycyclic compounds — 329
Helicenes — 329
Stereoselective helicene syntheses — 336
Other benzannulated PAHs —— 340
Twisted acenes —— 344
11 4
Circulenes and related curved polycyclic aromatic
hydrocarbons — 347
[5]-Circulenes — corannulenes — 347
[7]-Circulenes and related systems — 350
Cyctophanes and cyclophenylenes — 351
Cyclophanes — 352
Cycloparaphenylenes — 354
References — 361
Index — 365
|
| adam_txt |
Contents
Preface —V
List of abbreviations —— Xill
Introduction — aromatic compounds and aromaticity —1
Importance of aromatic compounds ——1
Synthetic dyes —1
Biologically active compounds ——-3
Aromatic compounds in materials science — 4
Aromaticity — 5
Stability of aromatic compounds — 6
Structure and reactivity of aromatic compounds — 8
Magnetic properties of aromatic compounds — 8
In this book — 10
References — 11
Electrophilic aromatic substitution — 13
Introduction — 13
General mechanistic principles — 13
Scope of electrophilic aromatic substitution — 13
Nitration — 14
Sulfonation — 15
Halogenation — 16
Carbon electrophiles: Friedel-Crafts alkylation and acylation — 17
Substituent effects in electrophilic aromatic substitution — 20
Reactivity — 20
Regioselectivity of electrophilic substitution of aromatic
compounds — 21
Regioselectivity in polysubstituted benzenes — 23
Functional group interconversion to control reactivity and
regioselectivity — 26
Reduction of nitro groups —— 26
Reduction of acyl groups —— 27
Reactions at benzylic positions — 28
Acylation of phenols and anilines —— 29
Reversibility of etectrophilic aromatic substitution —— 30
Protiodesilylation — 31
Halodesilylation — 31
Electrophilic rearrangement — the Fries rearrangement —— 32
2 8
Electrophilic aromatic substitution of polycyclic aromatic
compounds — 33
Electrophilic aromatic substitution of heteroaromatic
compounds — 34
Five-membered heterocycles — 34
Six-membered heterocycles — 36
Further reading — 36
References — 36
Nucleophilic aromatic substitution reactions — 39
introduction —— 39
Addition-elimination of nucleophiles (SyAr) —— 39
Leaving groups in SyAr — 41
Regioselectivity in SyAr reactions —— 41
Examples of the utility of SyAr reactions — 43
Carbon nucleophiles in nucleophilic aromatic substitution —— 45
Reversibility of SyAr reactions — 47
The Smiles rearrangement: an intramolecular SyAr reaction — 48
Substitution via benzyne formation — 51
Concerted nucleophilic aromatic substitutions — 52
Nucleophilic substitution of heteroaromatic systems — 55
Substitution of aryl diazonium salts — 58
Diazonium salt formation — 58
Reactions of diazonium salts with nucleophilic species — 58
Other reactions of aryl diazonium salts — 63
Formation of biaryls: the Gomberg-Bachmann reaction
and Pschorr cyclization — 65
References — 67
Reactions of aryllithium species — 73
Introduction —— 73
Deprotonation of arenes: directed ortho metalation —— 74
Introduction to directed ortho metalation —— 74
Examples of directed ortho metalation in synthesis —— 77
Anionic ortho-Fries rearrangement — 79
Directed remote metalation —— 8 amp;2
Lithium-halogen exchange — 85
Rearrangements of haloarenes: halogen dance reactions — 86
References — 92
5 Benzynes —— 95
5 1 Introduction to benzynes —— 95
5 2 Formation of benzynes — 95
521 Aryne formation by elimination of H-X — 96
522 Aryne formation from dihalobenzenes — 100
523 Aryne formation by elimination of small molecules — 101
524 Fluoride-induced aryne formation — 102
5 3 Reactions of arynes — 105
531 Cycloaddition reactions — 106
5 3 11 [4 + 2] Cycloaddition reactions — 106
5312 Intramolecular Diels-Alder reactions — 108
5313 [2+2] Cycloadditions — 109
5314 1,3-Dipolar cycloadditions — 111
532 Reactions of arynes with nucleophiles —— 113
5321 Nucleophilic addition reactions — 113
5322 Multicomponent reactions of arynes — 115
5323 Aryne insertion reactions — 116
533 Transition metal-mediated reactions of arynes — 121
5 4 Meta- and para-didehydrobenzenes (m- and p-arynes) — 125
References — 126
6 Transition-metal-mediated C-C bond forming reactions of aromatic
compounds — 131
6 1 Introduction — 131
6 2 Preparation of biaryls via homocoupling — 132
621 Copper-mediated coupling: the Ullmann reaction — 132
622 Nickel-mediated homocoupling reactions — 135
623 Oxidative coupling reactions — 138
6 3 Preparation of biaryls via cross-coupling reactions — 139
631 Metal-catalyzed cross-coupling — 139
6311 Ar-X cross-coupling precursors — 142
6312 Suzuki-Miyaura cross-coupling (aryl boronic acids or boronate
esters) — 143
6313 Negishi cross-coupling (organozinc) — 145
6314 Stille cross-coupling (organotin) — 146
6315 The Hiyama cross-coupling (organosilanes) — 148
6316 Kumada-Corriu cross-coupling (Grignard reagents) — 149
6 4 Other coupling reactions — 150
641 The Heck reaction — 150
642 The Sonogashira reaction — 153
643 Transition metal-mediated cyanation — 159
6 5 Direct arylation (C-H functionalization) — 160
6 5 1
Introduction to direct arylation — 160
Direct arylation with aryl halides — 161
Intramolecular direct arylation reactions with aryl halides — 162
Direct arylation using directing groups — 163
Direct arylation without directing groups — 166
Direct arylation of heteroaromatic compounds — 167
Direct arylation using organometallic species — 170
Direct arylation with arenes: dehydrogenative coupling — 171
Axially chiral biaryls: synthetic approaches — 174
Atropisomerism and axial chirality — 174
Approaches to racemic atropisomeric biaryls — 176
Stereoselective approaches to axially chiral biaryls — 177
References — 182
Other transition-metal-mediated reactions of aromatic
compounds — 191
Introduction — 191
Aromatic C-N and C-O bond formation — 191
Copper-catalyzed aryl C-N and C-O bond formation — 191
Palladium-catalyzed aryl amination — 195
Transition-metal-catalyzed borylation reactions — 200
Palladium-catalyzed borylation of aryl halides — 201
lridium-catalyzed direct borylation — 204
References — 211
Constructing aromatic rings — 215
Introduction — 215
Preparing benzene rings from non-aromatic precursors — 215
Cycloaddition reactions — 215
Transition metal-catalyzed alkyne cyclotrimerization — 218
Olefin metathesis — 224
Preparing aromatic heterocycles — 226
Five-membered ring heterocycles —- 227
Six-membered ring heterocycles — 230
Fused heteroaromatics — 234
Synthesis of indoles — 234
Synthesis of quinolines —— 239
Synthesis of isoquinolines — 242
References — 244
9
Fused aromatic rings — polycyclic aromatic hydrocarbons — 247
Introduction to polycyctic aromatic hydrocarbons —— 247
Classification and nomenclature of PAHs —— 247
Stability and reactivity of PAHs —— 250
The aromatic sextet —— 250
General reactivity of PAHs —— 253
Synthetic approaches to PAHs —— 256
Haworth synthesis — 256
The Pschorr synthesis —— 260
The Elbs reaction — 260
Diels-Alder cycloadditions — 261
The Wittig reaction — 266
Photocyclization (the Mallory-Katz reaction) — 267
Cyclodehydrogenation reactions — 268
Cyclodehydrohalogenation reactions — 275
Aryne cyclotrimerization and related reactions — 276
Ring-closing metathesis — 277
Alkyne benzannulation — 279
Asao-Yamamoto benzannualation — 282
References — 284
Synthesis of select classes of polycyclic aromatic hydrocarbons — 289
Introduction — 289
Synthesis of linear fused aromatic structures - the acenes — 289
Synthetic approaches to pentacenes — 290
Synthesis of larger acenes — 293
Synthesis of phenacenes — 295
Perylenes and rylenes — 299
Synthesis of triphenylenes and related compounds — 301
Triphenylenes — 301
Trinaphthylenes and larger starphenes — 306
From coronenes to larger PAHs — 311
Graphene nanoribbons — 317
References — 324
Nonplanar aromatic compounds — 329
Introduction — 329
Helicenes and related contorted polycyclic compounds — 329
Helicenes — 329
Stereoselective helicene syntheses — 336
Other benzannulated PAHs —— 340
Twisted acenes —— 344
11 4
Circulenes and related curved polycyclic aromatic
hydrocarbons — 347
[5]-Circulenes — corannulenes — 347
[7]-Circulenes and related systems — 350
Cyctophanes and cyclophenylenes — 351
Cyclophanes — 352
Cycloparaphenylenes — 354
References — 361
Index — 365 |
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| id | DE-604.BV048450628 |
| illustrated | Illustrated |
| index_date | 2024-07-03T20:30:37Z |
| indexdate | 2024-07-10T09:38:27Z |
| institution | BVB |
| isbn | 9783110562675 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-033828788 |
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| owner_facet | DE-19 DE-BY-UBM DE-11 |
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| publishDate | 2022 |
| publishDateSearch | 2022 |
| publishDateSort | 2022 |
| publisher | De Gruyter |
| record_format | marc |
| series2 | De Gruyter STEM |
| spelling | Maly, Kenneth E. Verfasser (DE-588)1267504412 aut Synthesis of aromatic compounds Kenneth E. Maly Berlin ; Boston De Gruyter [2022] XV, 372 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier De Gruyter STEM Aromatische Verbindungen Chemische Reaktion Organische Chemie Organische Synthese Erscheint auch als Online-Ausgabe 978-3-11-056268-2 HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033828788&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Maly, Kenneth E. Synthesis of aromatic compounds Aromatische Verbindungen Chemische Reaktion Organische Chemie Organische Synthese |
| title | Synthesis of aromatic compounds |
| title_auth | Synthesis of aromatic compounds |
| title_exact_search | Synthesis of aromatic compounds |
| title_exact_search_txtP | Synthesis of aromatic compounds |
| title_full | Synthesis of aromatic compounds Kenneth E. Maly |
| title_fullStr | Synthesis of aromatic compounds Kenneth E. Maly |
| title_full_unstemmed | Synthesis of aromatic compounds Kenneth E. Maly |
| title_short | Synthesis of aromatic compounds |
| title_sort | synthesis of aromatic compounds |
| topic | Aromatische Verbindungen Chemische Reaktion Organische Chemie Organische Synthese |
| topic_facet | Aromatische Verbindungen Chemische Reaktion Organische Chemie Organische Synthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033828788&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT malykennethe synthesisofaromaticcompounds |