Modern organic synthesis: an introduction
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| Main Authors: | , , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Hoboken, NJ
Wiley
2017
|
| Edition: | Second edition |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | xiii, 390 Seiten Illustrationen |
| ISBN: | 9781119086536 |
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MARC
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| 245 | 1 | 0 | |a Modern organic synthesis |b an introduction |c George S. Zweifel, Michael H. Nantz, Peter Somfai |
| 250 | |a Second edition | ||
| 264 | 1 | |a Hoboken, NJ |b Wiley |c 2017 | |
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Record in the Search Index
| _version_ | 1804177543798980608 |
|---|---|
| adam_text | Contents
About the Authors ix
Preface to the Second Edition xi
Preface to the First Edition xiii
1 Synthetic Design 1
1 1 Retrosynthetic Analysis 1
1 2 Reversal of the Carbonyl Group Polarity (Umpolung) 6
1 3 Steps in Planning a Synthesis 11
1 4 Choice of Synthetic Method 16
1 5 Domino Reactions (Cascade or Tandem Reactions) 18
1 6 Computer-Assisted Retrosynthetic Analysis 19
References 19
2 Stereochemical Considerations in Planning Syntheses 21
2 1 Conformational Analysis 21
2 2 Evaluation of Non-Bonded Interactions 25
2 3 Six-Membered Heterocyclic Systems 29
2 4 Polycyclic Ring Systems 30
2 5 Cyclohexyl Systems with sp2-Hybridized Atoms 33
2 6 Significant Energy Difference 35
2 7 Computer-Assisted Molecular Modeling 35
2 8 Reactivity and Product Determination as a Function of Conformation 36
References 42
3 The Concept of Protecting Functional Groups 45
3 1 Protection of N-H Groups 45
3 2 Protection of OH Groups 48
3 3 Protection of Diols as Acetals 55
3 4 Protection of Carbonyl Groups in Aldehydes and Ketones 56
3 5 Protection of the Carboxyl Group 62
3 6 Protection of Double Bonds 66
3 7 Protection of Triple Bonds 66
References 66
4 Functional Group Transformations 71
4 1 Oxidation of Alcohols to Aldehydes and Ketones 71
4 2 Reagents and Procedures for Alcohol Oxidation 72
4 3 Chemoselective Oxidizing Agents 76
4 4 Oxidation of Acyloins 79
4 5 Oxidation of Tertiary Allylic Alcohols 79
4 6 Oxidative Procedures to Carboxylic Acids 80
Contents
4 7 Allylic Oxidation of Alkenes 82
4 8 Terminology for Reduction of Carbonyl Compounds 85
4 9 Nucleophilic Reducing Agents 86
4 10 Electrophilic Reducing Agents 91
4 11 Regio-and Chemoselective Reductions 93
4 12 Diastereoselective Reductions of Cyclic Ketones 97
4 13 Inversion of Secondary Alcohol Stereochemistry 98
4 14 Diastereofacial Selectivity in Acyclic Systems 99
4 15 Enantioselective Reductions 104
References 108
5 Functional Group Transformations 115
5 1 Reactions of Carbon-Carbon Double Bonds 115
5 2 Reactions of Carbon-Carbon Triple Bonds 160
References 167
6 Formation of Carbon-Carbon Single Bonds via Enolate Anions 175
6 1 1,3-Dicarbonyl Compounds 175
6 2 Direct Alkylation of Enolates 185
6 3 Cyclization Reactions—Baldwin’s Rules for Ring Closure 193
6 4 Stereochemistry of Cyclic Ketone Alkylation 195
6 5 Imine and Hydrazone Anions 196
6 6 Enamines 197
6 7 The Aldol Reaction 199
6 8 Condensation Reactions of Enols and Enolates 213
6 9 Robinson Annulation 217
References 220
7 Formation of Carbon-Carbon Bonds via Organometallic Reagents 227
7 1 Organolithium Reagents 227
7 2 Organomagnesium Reagents 236
7 3 Organotitanium Reagents 239
7 4 Organocerium Reagents 240
7 5 Organocopper Reagents 241
7 6 Organochromium Reagents 251
171 Organozinc Reagents 252
7 8 Organoboron Reagents 256
7 9 Organosilicon Reagents 264
7 10 Organogold Chemistry 274
References 278
8 Palladium-Catalyzed Coupling Reactions 285
8 1 Palladium Oxidation State 285
8 2 Organic Synthesis with Palladium(O) Complexes 286
8 3 The Heck Reaction—Palladium(0)-Catalyzed Olefin Insertion Reactions 288
8 4 Palladium-Catalyzed Cross-Coupling with Organometallic Reagents 292
8 5 Cross-Coupling Reactions Involving sp-Carbons 301
8 6 The Trost-Tsuji Reaction 304
References 307
9 Formation of Carbon-Carbon n-Bonds 313
9 1 Formation of Carbon-Carbon Double Bonds 313
9 2 Formation of Carbon-Carbon Triple Bonds 343
References 350
10 Syntheses of Carbocyclic Systems 355
10 1 Intramolecular Free Radical Cyclizations 355
10 2 Cation-Jt Cyclizations 361
10 3 Pericyclic Reactions 364
10 4 Ring-Closing Olefin Metathesis 375
References 378
|
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| author | Zweifel, George S. 1926- Nantz, Michael H. 1958- Somfai, Peter 1960- |
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| author_sort | Zweifel, George S. 1926- |
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| discipline | Chemie / Pharmazie |
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| institution | BVB |
| isbn | 9781119086536 |
| language | English |
| lccn | 016054037 |
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| physical | xiii, 390 Seiten Illustrationen |
| publishDate | 2017 |
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| spelling | Zweifel, George S. 1926- Verfasser (DE-588)1134988621 aut Modern organic synthesis an introduction George S. Zweifel, Michael H. Nantz, Peter Somfai Second edition Hoboken, NJ Wiley 2017 xiii, 390 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Organic compounds Synthesis Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Präparative organische Chemie (DE-588)4121505-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Organische Verbindungen (DE-588)4043816-8 s Organische Synthese (DE-588)4075695-6 s 1\p DE-604 Präparative organische Chemie (DE-588)4121505-9 s 2\p DE-604 Nantz, Michael H. 1958- Verfasser (DE-588)173855369 aut Somfai, Peter 1960- Verfasser (DE-588)1134988842 aut Erscheint auch als Online-Ausgabe, pdf 978-1-119-08672-7 Erscheint auch als Online-Ausgabe, ePub 978-1-119-08676-5 HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029727036&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Zweifel, George S. 1926- Nantz, Michael H. 1958- Somfai, Peter 1960- Modern organic synthesis an introduction Organic compounds Synthesis Organische Verbindungen (DE-588)4043816-8 gnd Präparative organische Chemie (DE-588)4121505-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4121505-9 (DE-588)4075695-6 |
| title | Modern organic synthesis an introduction |
| title_auth | Modern organic synthesis an introduction |
| title_exact_search | Modern organic synthesis an introduction |
| title_full | Modern organic synthesis an introduction George S. Zweifel, Michael H. Nantz, Peter Somfai |
| title_fullStr | Modern organic synthesis an introduction George S. Zweifel, Michael H. Nantz, Peter Somfai |
| title_full_unstemmed | Modern organic synthesis an introduction George S. Zweifel, Michael H. Nantz, Peter Somfai |
| title_short | Modern organic synthesis |
| title_sort | modern organic synthesis an introduction |
| title_sub | an introduction |
| topic | Organic compounds Synthesis Organische Verbindungen (DE-588)4043816-8 gnd Präparative organische Chemie (DE-588)4121505-9 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Organic compounds Synthesis Organische Verbindungen Präparative organische Chemie Organische Synthese |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029727036&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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