Advanced Free Radical Reactions for Organic Synthesis
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Table of contents
- Copyright Pageiv
- Contentsix
- Prefacevii
- List of Abbreviationsxi
- Chapter 1. What are Free Radicals ?1
- 1.1 General aspects of free radicals1
- 1.2 Familiar and close radicals in our lives12
- 1.3 Stable free radicals15
- 1.4 Physical and chemical characteristics of free radicals20
- References36
- Chapter 2. Functional Group Conversion39
- 2.1 Radical coupling reactions39
- 2.2 Radical reduction42
- 2.3 Conversion to hydroxy groups and other functional groups48
- References54
- Chapter 3. Intramolecular Radical Cyclizations57
- 3.1 Cyclization to small-sized rings57
- 3.2 Cyclization to medium-sized and large-sized rings93
- 3.3 Ring expansions97
- 3.4 Cyclization to spiro skeleton106
- 3.5 Tandem cyclization to polycyclic rings110
- References115
- Chapter 4. Intermolecular Radical Addition Reactions123
- 4.1 Addition to olefins123
- 4.2 Allylation reactions137
- 4.3 Addition-cyclization reactions141
- 4.4 Reactions with carbon monoxide148
- 4.5 Addition to acetylenes150
- References153
- Chapter 5. Alkylation of Aromatics157
- 5.1 Oxidative conditions157
- 5.2 Non-oxidative conditions163
- 5.3 Photochemical conditions167
- 5.4 Others168
- References169
- Chapter 6. Intramolecular Hydrogen-Atom Abstraction171
- 6.1 Hydrogen-atom abstraction by oxygen-centered radicals: Barton reaction171
- 6.2 Hydrogen-atom abstraction by nitrogen-centered radicals: Hofmann-Löffler-Freytag reaction177
- 6.3 Hydrogen-atom abstraction by carbon-centered radicals180
- References183
- Chapter 7. Synthetic Uses of Free Radicals for Nucleosides and Sugars: Barton-McCombie Reaction187
- References196
- Chapter 8. Barton Decarboxylation Reaction with N-Hydroxy-2-thiopyridone199
- 8.1 Reduction200
- 8.2 Conversion to halides201
- 8.3 Conversion to chalcogenides203
- 8.4 Conversion to other functional groups204
- 8.5 Carbon-carbon bond formation205
- References212
- Chapter 9. Free Radical Reactions with Metal Hydrides215
- References218
- Chapter 10. Stereochemistry in Free Radical Reactions219
- 10.1 Reduction219
- 10.2 Carbon-carbon bond formation221
- References229
- Chapter 11. Free Radicals Related to Biology231
- 11.1 Vitamin B12231
- 11.2 Ene-diyne reactions: Bergman cyclization234
- 11.3 Radical 1,2-acyloxy transfer239
- References244
- Chapter 12. Free Radicals for Green Chemistry247
- 12.1 Design of free radical precursors247
- 12.2 Application of free radicals to environmentally benign synthesis249
- References255
- Index257
Free radical reactions have become increasingly important and a very attractive tool in organic synthesis in the last two decades, due to their powerful, selective, specific, and mild reaction abilities. Advanced Free Radical Reactions for Organic Synthesis reviews information on all types of practical radical reactions, e.g. cyclizations, additions, hydrogen-atom abstractions, decarboxylation reactions. The book usefully provides experimental details for the most important reactions as well as numerous references to the original literature. By covering both the fundamentals and synthetic applications it is therefore suitable for both new and experienced researchers, chemists, biochemists, natural product chemists and graduate students. This title is the definitive guide to radical chemistry for all scientists.
- Introduces and reviews the use of radicals to perform synthetic transformations.
- Practical details are provided for the most important methods.
- Numerous references to the original literature.
- Introduces and reviews the use of radicals to perform synthetic transformations.
- Practical details are provided for the most important methods.
- Numerous references to the original literature.