Reaction mechanisms in organic synthesis:
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Ames, Iowa
Wiley
2009
|
| Edition: | 1st ed |
| Series: | Postgraduate chemistry series
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Includes bibliographical references and index |
| Physical Description: | XX, 372 S. Ill. |
| ISBN: | 9781405150729 9781405190893 |
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| 100 | 1 | |a Parashar, Rakesh Kumar |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Reaction mechanisms in organic synthesis |c Rakesh K. Parashar |
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Record in the Search Index
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|---|---|
| adam_text | Titel: Reaction mechanisms in organic synthesis
Autor: Parashar, Rakesh Kumar
Jahr: 2009
Contents
Foreword xi
Preface xiii
About the Author xv
Acknowledgements xv
Abbreviations xvii
1 Synthetic Strategies 1
1.1 An introduction to organic synthesis 1
1.2 Retrosynthetic analysis (disconnection approach) 2
1.3 Umpolung strategy 6
1.4 Atom economy 8
1.5 Selectivity 10
1.5.1 Chemoselectivity 11
1.5.2 Regioselectivity 12
1.5.3 Stereoselectivity 13
1.5.4 Asymmetrie synthesis or chiral synthesis 16
1.6 Protecting groups 26
1.6.1 Common hydroxy protecting groups 27
1.6.2 Common diols protecting groups 36
1.6.3 Common amine protecting groups 38
1.6.4 Common carbonyl protecting groups 42
1.6.5 Common carboxylic aeid protecting groups 45
1.6.6 Common arenesulfonic aeid protecting groups 47
1.6.7 Common alkyne protecting groups 48
References 48
2 Reactive Intermediates 51
2.1 Carbocations 51
2.1.1 Structure and stability of carbocations 51
2.1.2 Generation of carbocations 53
2.1.3 Reactions of carbocations 54
2.1.4 Non-classical carbocations 60
2.2 Carbanions 63
2.2.1 Structure and stability of carbanions 63
2.2.2 Generation of carbanions 65
2.2.3 Reactions of carbanions 65
2.3 Free radicals 70
2.3.1 Structure and stability of free radicals 71
2.3.2 Generation of free radicals 72
vii
viii Contents
2.3.3 Radical ions 76
2.3.4 Reactionsofradicals 77
2.4 Carbenes 90
2.4.1 Structure and stabilityof carbenes 92
2.4.2 Generation of carbenes 93
2.4.3 Reactions of carbenes 95
2.5 Nitrenes 101
2.5.1 Structure and stabilityof nitrenes 101
2.5.2 Generation of nitrenes 101
2.5.3 Reactions of nitrenes 102
2.6 Benzynes 105
2.6.1 Generation of benzynes 105
2.6.2 Reactions of benzynes 106
References 109
3 Stabilized Carbanions, Enamines and Ylides 112
3.1 Stabilized carbanions 112
3.1.1 Reaction of stabilized carbanions (enolates) with alkyl halides
(enolate alkylation) 114
3.1.2 Reaction of stabilized carbanions with carbonyl compounds 118
3.1.3 Conjugate addition of enolate to et, ß-unsaturated carbonyl
compounds 125
3.1.4 Reaction of enolates with iminium ions orimines 127
3.2 Enamines 130
3.3 Ylides 134
3.3.1 Formation of ylides 135
3.3.2 Reactions of ylides 137
3.3.3 Asymmetrie ylide reactions 142
References 146
4 Carbon-Carbon Double Bond Forming Reactions 148
4.1 Introduction 148
4.2 Elimination reactions 148
4.2.1 ß-Eliminations 148
4.2.2 Unimolecular syn-eliminations 153
4.2.3 Reactions from epoxides, thionocarbonates and episulfides 156
4.3 Alkenation (alkylidenation) of carbonyl compounds 157
4.3.1 Wittig reactions 158
4.3.2 Julia alkenation and modified Julia alkenation (Julia-Kocienski
alkenation) 166
4.3.3 Peterson reaction 172
4.3.4 Use of titanium-based reagents 174
4.3.5 Use of Zinc (Zn) and Zirconium (Zr) reagents for the alkenation
of ketones and aldehydes 182
4.3.6 Bamford-Stevens reaction and Shapiro reaction 184
4.3.7 Barton-Kellogg reaction 185
4.3.8 Catalytic aldehyde and ketone alkenation 187
4.4 Reduction of alkynes 188
References 189
Contents ix
5 Transition Metal-Mediated Carbon-Carbon Bond Forming Reactions 191
5.1 Carbon-carbon bond forming reactions catalyzed by transition metals 193
5.1.1 Heckreaction 193
5.1.2 Allylic substitutions 198
5.1.3 Cu-and Ni-catalyzed couplings 201
5.2 Transition metal-catalyzed coupling of organometallic reagents with
organic halides and related electrophiles 203
5.2.1 Coupling of Grignard reagents 205
5.2.2 Coupling of organostannanes 208
5.2.3 Coupling oforganoboranes 211
5.2.4 Coupling of organosilanes 213
5.2.5 Coupling of organocopper reagents 215
5.2.6 Coupling of organozinc compounds 216
References 222
6 Reduction 224
6.1 Reduction of carbon-carbon double bond 224
6.1.1 Catalytic hydrogenation 224
6.1.2 Hydrogen transfer reagents 228
6.2 Reduction of acetylenes 229
6.2.1 Catalytic hydrogenation 229
6.2.2 Dissolving metals 230
6.2.3 Metal hydrides 230
6.2.4 Hydroboration-protonation 231
6.3 Reduction ofbenzene and derivatives 231
6.3.1 Catalytic hydrogenation 231
6.3.2 Birch reduction 232
6.4 Reduction of carbonyl compounds 234
6.4.1 Catalytic hydrogenation 234
6.4.2 Metal hydrides 236
6.4.3 Metal and proton source 253
6.4.4 Hydrogen transfer reagents 255
6.5 Reduction of a, ß-unsaturated aldehydes and ketone 258
6.5.1 Catalytic hydrogenation 258
6.5.2 Hydride reagents 258
6.5.3 Dissolving metals 260
6.6 Reduction of nitro, N-oxides, oximes, azides, nitriles and nitroso
compounds 261
6.6.1 Catalytic hydrogenation 261
6.6.2 Metal hydrides 261
6.6.3 Metal and proton source 263
6.6.4 Triphenylphosphine 264
6.7 Hydrogenolysis 265
References 266
7 Oxidation 268
7.1 Oxidation of alcohols 268
7.1.1 Chromium(VI) 268
7.1.2 Potassium permanganate 272
x Contents
7.1.3 Manganesedioxide (MnO2) 273
7.1.4 Dimethylsulfoxide-mediated oxidations 274
7.1.5 Dess-Martin periodinane (DMP) 278
7.1.6 Tetra-ra-propylammonium perruthenate (TPAP) 279
7.1.7 Silver oxide and silver carbonate 280
7.1.8 Oppenauer oxidation 281
7.2 Oxidation ofaldehydes and ketones 283
7.3 Oxidation of phenols 288
7.4 Epoxidation 291
7.5 Dihydroxylation 297
7.6 Aminohydroxylation 301
7.7 OxidativecleavageofC-C double bonds 302
7.7.1 Ozonolysis 303
7.7.2 Glycol cleavage 304
7.8 Oxidation of anilines 306
7.9 Dehydrogenation 307
7.10 Allylic or benzylic oxidation 308
7.11 Oxidation of sulfides 308
7.12 Oxidation ofaliphatic side chains attached to aromatic ring 309
References 311
8 Pericyclic Reactions 313
8.1 Important classes of pericyclic reactions 313
8.1.1 Cycloaddition reactions 313
8.1.2 Electrocyclic reactions 314
8.1.3 Sigmatropic rearrangements 314
8.1.4 Ene reactions 314
8.1.5 Other classes of pericyclic reactions 314
8.2 Theoretical explanation of pericyclic reactions 316
8.2.1 MOs and their symmetry properties 316
8.2.2 Suprafacial and antarafacial 322
8.2.3 Conservation of orbital symmetry 324
8.3 Cycloaddition reactions 327
8.3.1 [4+2]-Cycloaddition reactions 328
8.3.2 [2+2]-Cycloaddition reactions 331
8.3.3 1,3-Dipolaradditions 332
8.3.4 Theoretical explanation 332
8.4 Electrocyclic reactions 340
8.4.1 Theoretical explanation 342
8.4.2 General rules for electrocyclic reactions 349
8.5 Sigmatropic rearrangements 349
8.5.1 Analysis of sigmatropic rearrangements 355
8.5.2 Carbon shift 358
8.6 Ene reactions 360
8.7 Selection rules 362
References 362
Index 364
|
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| id | DE-604.BV035456144 |
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| indexdate | 2024-07-09T21:35:40Z |
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| language | English |
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| physical | XX, 372 S. Ill. |
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| spelling | Parashar, Rakesh Kumar Verfasser aut Reaction mechanisms in organic synthesis Rakesh K. Parashar 1st ed Ames, Iowa Wiley 2009 XX, 372 S. Ill. txt rdacontent n rdamedia nc rdacarrier Postgraduate chemistry series Includes bibliographical references and index Composés organiques - Synthèse ram Réactions chimiques organiques - Mécanismes ram Organic compounds Synthesis Organic reaction mechanisms Physical organic chemistry Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Reaktionsmechanismus (DE-588)4177123-0 s Organische Synthese (DE-588)4075695-6 s DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017376082&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Parashar, Rakesh Kumar Reaction mechanisms in organic synthesis Composés organiques - Synthèse ram Réactions chimiques organiques - Mécanismes ram Organic compounds Synthesis Organic reaction mechanisms Physical organic chemistry Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4177123-0 (DE-588)4075695-6 |
| title | Reaction mechanisms in organic synthesis |
| title_auth | Reaction mechanisms in organic synthesis |
| title_exact_search | Reaction mechanisms in organic synthesis |
| title_full | Reaction mechanisms in organic synthesis Rakesh K. Parashar |
| title_fullStr | Reaction mechanisms in organic synthesis Rakesh K. Parashar |
| title_full_unstemmed | Reaction mechanisms in organic synthesis Rakesh K. Parashar |
| title_short | Reaction mechanisms in organic synthesis |
| title_sort | reaction mechanisms in organic synthesis |
| topic | Composés organiques - Synthèse ram Réactions chimiques organiques - Mécanismes ram Organic compounds Synthesis Organic reaction mechanisms Physical organic chemistry Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Composés organiques - Synthèse Réactions chimiques organiques - Mécanismes Organic compounds Synthesis Organic reaction mechanisms Physical organic chemistry Reaktionsmechanismus Organische Synthese |
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