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| ADVANCED FREE RADICAL REACTIONS FOR ORGANIC SYNTHESIS
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By
Hideo Togo, Department of Chemistry, Faculty of Science, Chiba University, Japan
Description
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.
Audience
for new and experienced researchers, chemists, biochemists, natural product chemists and graduate students.
Contents
1. What are Free Radicals?
General Aspects of Free Radicals.
-Aspects of free radicals.
-Types of free radicals.
-Reaction
style of radicals.
-Orientation in radical additions.
-Reactivity in radical additions.
-Reaction patterns of radicals.
-Generation of
radicals.
Familiar and Close Radicals in Our Lives.
Stable Free Radicals.
Physical and Chemical Characteristics of Free Radicals.
-Orbital
interactions between radicals and olefins.
-Baldwin's rule.
-Rate constants in radical reactions.
2. Functional Group Conversion
Radical Coupling Reactions.
Radical Reduction.
Conversion to Hydroxy Group and Other Functional Groups.
3. Intramolecular Radical
Cyclizations
Cyclization to Small-Sized Rings.
-Cyclization onto olefinic group and acetylenic group by sp3 carbon-centered
radicals.
-Cyclization onto Olefinic Group and Aromatic Group by sp2 Carbon-Centered Radicals.
-Generation of sp carbon-centered
radicals.
-Cyclization onto carbonyl group by sp3 or sp2 carbon-centered radicals and other related cyclizations.
Cyclization to Medium-Sized and Large-Sized Rings.
Ring Expansions.
Cyclization to Spiro Skeleton.
Tandem Cyclization to Polycyclic Rings.
4. Intermolecular Radical Addition Reactions
Addition to Olefins.
-Reductive conditions.
-Oxidative conditions.
-Photochemical
conditions.
-Addition-elimination reactions.
Allylation Reactions.
Addition-Cyclization Reactions.
Reactions with Carbon Monoxide.
Addition
to Acetylenes.
5. Alkylation of Aromatics
Oxidative Conditions.
Non-Oxidative Conditions.
Photochemical Conditions.
Others.
6. Intramolecular Hydrogen-Atom Abstraction
Hydrogen-atom Abstraction by Oxygen-Centered Radicals: Barton Reaction.
Hydrogen-atom Abstraction by Nitrogen-Centered Radicals: Hofmann-L ffler-Freytag Reaction.
Hydrogen-atom Abstraction by Carbon-Centered
Radicals.
7. Synthetic Uses of Free Radicals for Nucleosides and Sugars: Barton-McCombie Reaction
8. Barton
Decarboxylation Reaction with N-hydroxy-2-thiopyridone
Reduction.
Conversion to Halides.
Conversion to Chalcogenides.
Conversion to Other Functional Groups.
Carbon-Carbon Bond Formation.
-Intramolecular radical cyclization.
-Intermolecular coupling reaction.
-Intermolecular addition reaction.
-Alkylation of aromatics.
-Others.
9. Free Radical Reactions with Metal Hydrides
10. Stereochemistry in Free Radical Reactions
Reduction.
Carbon-Carbon Bond Formation.
11. Free Radicals Related
to Biology
Vitamin B12.
Ene-diyne Reactions: Bergman Cyclization.
Radical 1,2-Acyloxy Transfer.
12. Free
Radicals for Green Chemistry
Design of Free Radical Precursors.
Application of Free Radicals to Environmentally Benign Synthesis.
| Bibliographic details |
Hardbound, 270 pages, publication date: JAN-2004
ISBN-13: 978-0-08-044374-4
ISBN-10: 0-08-044374-5
Imprint: ELSEVIER
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| Price and Ordering |
Price:
GBP 151.99
USD 250
EUR 178.95
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Last update: 30 Nov 2009
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