Advanced Free Radical Reactions for Organic Synthesis

Advanced Free Radical Reactions for Organic Synthesis

1st Edition - January 14, 2004
This is the Latest Edition
  • Author: Hideo Togo
  • eBook ISBN: 9780080524252

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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.

Key Features

  • 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

Table of 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

    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
    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

Product details

  • No. of pages: 270
  • Language: English
  • Copyright: © Elsevier Science 2004
  • Published: January 14, 2004
  • Imprint: Elsevier Science
  • eBook ISBN: 9780080524252
  • About the Author

    Hideo Togo

    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.

    Affiliations and Expertise

    Department of Chemistry, Faculty of Science, Chiba University, Japan