Pericyclic reactions - a textbook: reactions, applications and theory
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2005
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XIV, 418 S. zahlr. graph. Darst. |
| ISBN: | 9783527314393 3527314393 |
Internformat
MARC
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Datensatz im Suchindex
| _version_ | 1804142444989644800 |
|---|---|
| adam_text | CONTENTS
Foreword V
Preface XIII
1 MOLECULAR ORBITALS AND THEIR SYMMETRY 1
1.1 Molecular Orbitals 1
1.2 Molecular Orbitals of Conjugated Polyene Systems 4
1.3 Symmetry Elements and Symmetry Operations 6
1.4 Definition and Classification of Pericyclic Reactions 6
1.4.1 Electrocyclic Ring Closure and Ring Opening Reactions 9
1.4.2 Cycloaddition and Cycloreversion Reactions 9
1.4.3 Sigmatropic Rearrangements 9
1.4.4 Chelotropic Reactions 9
1.4.5 Group Transfer Reactions 10
1.5 Methods of Analyzing Pericyclic Reactions 10
1.5.1 Orbital Symmetry Correlation Method 11
1.5.2 Frontier Orbital Method 13
1.5.3 Transition State Aromaticity Method 14
References 17
2 ELECTROCYCLIC REACTIONS 19
2.1 Definition of Electrocyclic Reactions 19
2.2 Classification of Electrocyclic Reactions 19
2.3 Stereochemistry of Electrocyclic Reactions 20
2.4 Woodward-Hoffmann Rules for Electrocyclic Reactions 21
2.4.1 Frontier Orbital Method of Analysis of Electrocyclic Reactions 21
2.4.2 Orbital Symmetry Correlation Method for the Electrocyclic Reactions 23
2.4.3 Transition State Aromaticity Method 31
2.5 Electrocyclic Reactions Exemplified 32
2.5.1 Three-membered Ring Systems 32
2.5.2 Four-membered Ring Systems 37
VIII Contents
2.5.3 Five-membered Ring Systems 48
2.5.4 Six-membered Ring Systems 57
2.5.5 Seven-membered Ring Systems 67
2.5.6 Eight-membered Ring Systems 69
2.5.7 Miscellaneous Higher Order Systems 71
References 75
3 CYCLOADDITION REACTIONS 82
3.1 Definition 82
3.2 Classification 82
3.3 Stereochemistry of Cycloaddition Reactions 83
3.4 Woodward-Hoffmann Rules for Cycloaddition Reactions 84
3.4.1 Frontier Orbital Method 84
3.4.2 Orbital Correlation Method 86
3.4.3 Transition State Aromaticity Method 90
3.5 Illustrations of Cycloaddition Reactions 90
3.5.1 [2n + 2n] Cycloadditions 90
3.5.2 Photochemical [2n + 2ti] Cycloadditions 91
3.5.3 Thermal [2tis + 27ia] Cycloadditions 98
3.5.4 Intramolecular Cycloaddition Reactions of Ketenes 102
3.6 [4n + 2n] Cycloaddition Reactions 106
3.6.1 Diels-Alder Reaction 106
3.6.2 Diels-Alder Dienes 107
3.6.3 Dienophiles 109
3.6.4 The cis Rule 109
3.6.5 Alder s endo Rule 111
3.6.6 Regioselectivity 114
3.6.7 Rates of Diels-Alder Reactions 117
3.6.8 Diels-Alder Reaction in Organic Synthesis 119
3.6.9 Heterodienes and Dienophiles 139
3.6.10 Inverse Electron Demand Diels-Alder (IEDDA) Reactions 146
3.6.11 Intramolecular Diels-Alder (IDA) Reactions 150
3.6.12 Catalysis of Diels-Alder Reaction 157
Contents IX
3.6.13 Asymmetric Diels-Alder Reactions 161
3.7 1,3-DipolarCycloadditions 169
3.7.1 Mechanism of 1,3-Dipolar Cycloadditions 171
3.8 Synthetic Applications of 1,3-Dipolar Cycloadditions 172
3.8.1 Nitrones 172
3.8.2 Azomethine ylids 179
3.8.3 Nitrile oxides 185
3.9 Higher order cycloaddition reactions 191
3.9.1 [4n + 4?t] Cycloadditions 191
3.9.2 [6tt + 4n] Cycloadditions 193
3.9.3 [8n + 27t] Cycloadditions 195
3.9.4 [14n + 2n] Cycloadditions 196
References 197
4 SIGMATROPIC REARRANGEMENTS 215
4.1 Definition 215
4.2 Classification 215
4.3 Stereochemistry of Sigmatropic Rearrangements 217
4.4 Woodward-Hoffmann Rules for Sigmatropic Rearrangements 218
4.4.1 Frontier Orbital Method 218
4.4.2 Transition State Aromaticity Method 222
4.5 Illustrations of Sigmatropic Rearrangements 225
4.5.1 [1,2]-Sigmatropic Rearrangements of Carbenium Ions 225
4.5.2 [1,3] Sigmatropic Rearrangements 225
4.5.3 [1,4] Sigmatropic Rearrangements 233
4.5.4 [1,5] Sigmatropic Rearrangements 235
4.5.5 [3.3] Sigmatropic Rearrangements 241
4.5.6 Degenerate Cope Systems 245
4.5.7 Claisen Rearrangement 257
4.5.7.1 Mechanism of Claisen Rearrangement 259
4.5.7.2 Aromatic Claisen Rearrangement 268
4.5.8 Asymmetric [3,3] Sigmatropic Rearrangements 271
4.5.9 [2,3] Sigmatropic Rearrangements 279
X Contents
4.5.10 Higher Order Sigmatropic Rearrangements 292
References 297
5 CHELOTROPIC, GROUP TRANSFER AND ENE REACTIONS 308
CHELOTROPIC REACTIONS 308
5.1 Definition Chelotropic Reactions 308
5.2 Analysis of the Chelotropic Reactions 309
5.3 Woodward-Hoffmann Rules for Chelotropic Reactions 309
5.4 Chelotropic Reactions Exemplified 312
5.4.1 Reactions Involving SO2 312
5.4.2 Synthetic Applications 319
5.4.3 Chelotropic Extrusion of Nitrogen 321
5.4.4 Chelotropic Decarbonylation of Ketones 322
5.4.5 Chelotropic Trapping of Nitric Oxide 325
5.4.6 Miscellaneous Systems 326
GROUP TRANSFER REACTIONS 326
5.5 Definition of Group Transfer Reactions 326
5.5.1 Group Transfer Reactions Exemplified 328
ENE REACTIONS 329
5.6 Definition of Ene Reactions 329
5.6.1 Classification 330
5.6.2 Uncatalyzed all-carbon Ene Reactions 331
5.6.3 Uncatalyzed Intramolecular all-carbon Ene Reactions 333
5.6.4 Lewis acid Catalyzed Ene Reactions 336
5.6.5 Oxy-ene and Anionic Oxy-ene Reactions 337
5.6.6 Carbonyl ene reactions 338
5.6.7 Lewis Acid Catalyzed Carbonyl Ene Reactions 340
5.6.8 Imino-ene Reactions 343
5.6.9 Singlet Oxygen Ene Reactions 346
5.6.10 Stereochemistry of Ene Reactions - Diastereoselection 346
5.6.11 Asymmetric Ene Reactions 349
5.6.12 Retro Ene Reactions 353
References 354
Contents XI
6 SPECIAL TOPICS 361
6.1 Organometallic Pericyclic Reactions 361
6.1.1 Introduction 361
6.1.2 Electrocyclic Reactions 361
6.1.3 Sigmatropic Rearrangements 365
6.1.4 Cycloaddition Reactions 3 70
6.1.5 Organometallic Ene Reactions 373
6.2 Pericyclic Reactions of Radical Cations 374
6.2.1 Introduction 374
6.2.2 Generation of Radical Cations 375
6.2.3 Electrocyclic Reactions 377
6.2.4 Radical Cation Cycloadditions 380
6.2.5 Radical Cation Cyclobutanation Reactions 381
6.2.6 Radical Cation Diels-Alder Reactions 385
6.3 Periselectivity 393
6.3.1 Definition 393
6.3.2 Examples of Periselectivity 393
6.4 Symmetry Forbidden Concerted Processes:
Violation of Woodward-Hoffmann Rules? 399
6.4.1 Introduction 399
6.4.2 Examples of Symmetry Forbidden Reactions 400
References 405
Subject Index 411
Author Index 417
|
| any_adam_object | 1 |
| author | Sankararaman, Sethuraman 1957- |
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| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.2 |
| dewey-search | 547.2 |
| dewey-sort | 3547.2 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| indexdate | 2024-07-09T22:31:52Z |
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| isbn | 9783527314393 3527314393 |
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| spelling | Sankararaman, Sethuraman 1957- Verfasser (DE-588)130303763 aut Pericyclic reactions - a textbook reactions, applications and theory S. Sankararaman Weinheim Wiley-VCH 2005 XIV, 418 S. zahlr. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Pericyclische Reaktion (DE-588)4173761-1 gnd rswk-swf Pericyclische Reaktion (DE-588)4173761-1 s DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=019989089&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
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| title | Pericyclic reactions - a textbook reactions, applications and theory |
| title_auth | Pericyclic reactions - a textbook reactions, applications and theory |
| title_exact_search | Pericyclic reactions - a textbook reactions, applications and theory |
| title_full | Pericyclic reactions - a textbook reactions, applications and theory S. Sankararaman |
| title_fullStr | Pericyclic reactions - a textbook reactions, applications and theory S. Sankararaman |
| title_full_unstemmed | Pericyclic reactions - a textbook reactions, applications and theory S. Sankararaman |
| title_short | Pericyclic reactions - a textbook |
| title_sort | pericyclic reactions a textbook reactions applications and theory |
| title_sub | reactions, applications and theory |
| topic | Pericyclische Reaktion (DE-588)4173761-1 gnd |
| topic_facet | Pericyclische Reaktion |
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