Advanced Free Radical Reactions for Organic Synthesis (eBook)

eBook Download: PDF

2004 | 1. Auflage
270 Seiten
Elsevier Science (Verlag)
978-0-08-052425-2 (ISBN)

Infos

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.

Inhalt

Front Cover 1
Advanced Free Radical Reactions for Organic Synthesis 4
Copyright Page 5
Contents 10
Preface 8
List of Abbreviations 12
Chapter 1. What are Free Radicals ? 14
1.1 General aspects of free radicals 14
1.2 Familiar and close radicals in our lives 25
1.3 Stable free radicals 28
1.4 Physical and chemical characteristics of free radicals 33
References 49
Chapter 2. Functional Group Conversion 52
2.1 Radical coupling reactions 52
2.2 Radical reduction 55
2.3 Conversion to hydroxy groups and other functional groups 61
References 67
Chapter 3. Intramolecular Radical Cyclizations 70
3.1 Cyclization to small-sized rings 70
3.2 Cyclization to medium-sized and large-sized rings 106
3.3 Ring expansions 110
3.4 Cyclization to spiro skeleton 119
3.5 Tandem cyclization to polycyclic rings 123
References 128
Chapter 4. Intermolecular Radical Addition Reactions 136
4.1 Addition to olefins 136
4.2 Allylation reactions 150
4.3 Addition-cyclization reactions 154
4.4 Reactions with carbon monoxide 161
4.5 Addition to acetylenes 163
References 166
Chapter 5. Alkylation of Aromatics 170
5.1 Oxidative conditions 170
5.2 Non-oxidative conditions 176
5.3 Photochemical conditions 180
5.4 Others 181
References 182
Chapter 6. Intramolecular Hydrogen-Atom Abstraction 184
6.1 Hydrogen-atom abstraction by oxygen-centered radicals: Barton reaction 184
6.2 Hydrogen-atom abstraction by nitrogen-centered radicals: Hofmann-Löffler-Freytag reaction 190
6.3 Hydrogen-atom abstraction by carbon-centered radicals 193
References 196
Chapter 7. Synthetic Uses of Free Radicals for Nucleosides and Sugars: Barton-McCombie Reaction 200
References 209
Chapter 8. Barton Decarboxylation Reaction with N-Hydroxy-2-thiopyridone 212
8.1 Reduction 213
8.2 Conversion to halides 214
8.3 Conversion to chalcogenides 216
8.4 Conversion to other functional groups 217
8.5 Carbon-carbon bond formation 218
References 225
Chapter 9. Free Radical Reactions with Metal Hydrides 228
References 231
Chapter 10. Stereochemistry in Free Radical Reactions 232
10.1 Reduction 232
10.2 Carbon-carbon bond formation 234
References 242
Chapter 11. Free Radicals Related to Biology 244
11.1 Vitamin B12 244
11.2 Ene-diyne reactions: Bergman cyclization 247
11.3 Radical 1,2-acyloxy transfer 252
References 257
Chapter 12. Free Radicals for Green Chemistry 260
12.1 Design of free radical precursors 260
12.2 Application of free radicals to environmentally benign synthesis 262
References 268
Index 270

Produkt-Details

• Erscheint lt. Verlag: 14.1.2004
• Sprache: englisch
• Themenwelt: Sachbuch/Ratgeber
• Themenwelt: Naturwissenschaften ► Biologie ► Biochemie
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik
• ISBN-10: 0-08-052425-7 / 0080524257
• ISBN-13: 978-0-08-052425-2 / 9780080524252