Simpkins / Perlmutter Sulphones in Organic Synthesis

1. Auflage 2013
ISBN: 978-1-4832-9279-3
Verlag: Elsevier Science & Techn.
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, Band Volume 10, 394 Seiten, Web PDF

Reihe: Tetrahedron Organic Chemistry

Over the last twenty years the use of sulphones in organic synthesis has increased dramatically, the synthetic repertoire of sulphones having been developed to such an extent as to rival the carbonyl functionality for versatility. Not only have sulphones been employed in a great many synthetic methodologies, enabling the preparation of a vast array of functionalised products, but the sulphone group has also proved to be of enormous value in many of the most demanding and sophisticated total syntheses carried out in recent years. This book describes in detail all of the important sulphone chemistry employed in organic synthesis, ranging from the well-established sulphone-mediated methods to less familiar sulphone reactions and very recent discoveries of synthetic potential.

Autoren/Hrsg.

Simpkins, N S.

Perlmutter, Patrick

Inhaltsverzeichnis

1;Front Cover;1
2;Sulphones in Organic Synthesis;4
3;Copyright Page;5
4;Table of Contents;8
5;Preface;6
6;CHAPTER 1. Introduction to Sulphone Chemistry;14
6.1;References;17
7;CHAPTER 2. The Preparation of Sulphones;18
7.1;2.1 Simple Alkyl Aryl and Dialkyl Sulphones;18
7.2;2.2 Vinyl Sulphones;34
7.3;2.3 Allylic, Allenic, Alkynyl and Aryl Sulphones;53
7.4;2.4 Functionalised Sulphones;64
8;CHAPTER 3. Sulphonyl Carbanions;113
8.1;3.1 Introduction to Sulphonyl Carbanions;113
8.2;3.2 Reactions of Simple Sulphonyl Carbanions;124
8.3;3.3 Reactions of Additionally Stabilised Sulphonyl Carbanions;157
8.4;3.4 Sulphonyl Polyanions;171
9;CHAPTER 4. Additions to Unsaturated Sulphones;196
9.1;4.1 Heteroatom Nucleophiles;196
9.2;4.2 Non-stabilised Organometallics;202
9.3;4.3 Enolates, Related Anions and Miscellaneous Carbon Nucleophiles;207
9.4;4.4 Cyclopropanations;211
9.5;4.5 Radical Additions;213
10;CHAPTER 5. Rearrangements of Sulphones;220
10.1;5.1 Ring Expansions and Fragmentations;220
10.2;5.2 Sulphinate to Sulphone Rearrangements;225
10.3;5.3 1,3-Rearrangements of Allylic Sulphones;229
10.4;5.4 The Truce-Smiles Rearrangement;233
10.5;5.5 Miscellaneous Rearrangements;235
11;CHAPTER 6. Cycloaddition Chemistry of Unsaturated Sulphones;240
11.1;6.1 [2+2] Cycloadditions;240
11.2;6.2 [3+2] Cycloadditions;243
11.3;6.3 [4+2] Cycloadditions;249
12;CHAPTER 7. Carbon-Carbon Double-Bond Formation by Sulphone Elimination;267
12.1;7.1 The Julia Olefination Reaction;267
12.2;7.2 Alternative ß-Eliminations of Sulphones;275
12.3;7.3 The Ramberg-Bäcklund Reaction;286
13;CHAPTER 8. Chemistry of Cyclic Sulphones;303
13.1;8.1 Three-membered Ring Sulphones;304
13.2;8.2 Four-membered Ring Sulphones;311
13.3;8.3 Five-membered Ring Sulphones;320
13.4;8.4 Functionalised Normal-sized Rings;336
13.5;8.5 Larger Ring Sulphones;339
14;CHAPTER 9. Desulphonylation;347
14.1;9.1 Simple Alkyl Aryl and Dialkyl Sulphones;347
14.2;9.2 Allylic Sulphones;354
14.3;9.3 Vinyl Sulphones;361
14.4;9.4 Functionalised Sulphones;367
14.5;9.5 Sulphone Reduction;378
15;INDEX;386