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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
New and experienced researchers, chemists, biochemists, natural product chemists and graduate students
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
-Rate constants in radical reactions
2. Functional Group Conversion
Radical Coupling Reactions
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
Cyclization to Spiro Skeleton
Tandem Cyclization to Polycyclic Rings
4. Intermolecular Radical Addition Reactions
Addition to Olefins
Reactions with Carbon Monoxide
Addition to Acetylenes
5. Alkylation of Aromatics
6. Intramolecular Hydrogen-Atom Abstraction
Hydrogen-atom Abstraction by Oxygen-Centered Radicals: Barton Reaction
Hydrogen-atom Abstraction by Nitrogen-Centered Radicals: Hofmann-Löffler-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
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
9. Free Radical Reactions with Metal Hydrides
10. Stereochemistry in Free Radical Reactions
Carbon-Carbon Bond Formation
11. Free Radicals Related to Biology
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
- No. of pages:
- © Elsevier Science 2004
- 14th January 2004
- Elsevier Science
- Hardcover ISBN:
- eBook ISBN:
Dr. Togo obtained his Ph. D in 1983 under the supervision of Professor Shigeru Oae (sulfur chemist) at Tsukuba University. He became a post-doctoral fellow at University of Lausanne in Switzerland (1983 to 1984) and ICSN in CNRS (The late Professor Sir Derek H. R. Barton; Novel-Prize Winner) in France (1984 to 1985). He became a research associate at Tsukuba University in 1987 and then at the present university in 1989, where he became an associate professor in 1994 and then a full professor since 2005. His research interests are the chemistry of novel reactions with molecular iodine and trivalent iodines, and with free radicals for organic synthesis.
Department of Chemistry, Faculty of Science, Chiba University, Japan
"The author has succeeded in presenting many facets of this very interesting area of chemistry in a highly engaging manner. As a result, anyone who wishes to familiarize themselves with the field of radical chemistry should take the time to look through Advanced Free Radical Reactions for Organic Synthesis." --ORGANIC CHEMISTRY, 2005
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