Hypervalent Iodine in Organic Synthesis

1st Edition

Print ISBN: 9780123909480
eBook ISBN: 9780080534367
Imprint: Academic Press
Published Date: 14th November 1996
Page Count: 223
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This book describes the fascinating chemistry of the many kinds of organic compounds of hypervalent iodine. Each chapter deals with a particular iodine compound or families of compounds which have been used as reagents in a plethora of useful transformations. These include assorted oxidation, such as with the precious Dess-Martin reagent as well as with a wide range of further reactions. Prominent features of hypervalent iodine reagents derived from iodobenzene are: ready availability, operational simplicity, mild reaction conditions, and high efficiency. They are environmentally safe and can be recycled. New species may be easily prepared by introducing substituents in the benzene ring or changing the ligand attached to iodine. Their combination with other reagents broadens considerably their synthetic potential. Today, no synthetic chemist can afford to ignore the valuable hypervalentiodine reagents.

Key Features

@introbul:Key Features @bul:* Features up-to-date coverage of a wide range of topics

  • Includes many tables featuring a diversity of reactivity, and a comprehensive index
  • Acts as a comprehensive, up-to-date reference on all aspects of hypervalent iodine chemistry
  • Contains a section on unusual efficiency of hypervalent iodine reactions


Organic chemists in industry and academia, especially those working with iodine compounds

Table of Contents

Foreword. Preface. General Considerations. Preparative Methods for Hypervalent Iodine Reagents. (Diacetoxyiodo)benzene. [Bis(acyloxy)iodo]arenes. Iodosylbenzene. (Difluoroiodo)-and (dichloroiodo)arenes. [Hydroxy(tosyloxy)iodo]benzene and Its Analogues. Diaryliodonium Salts. Phenyliodonium Salts with an Aliphatic Moiety. Phenyliodonium Zwitterions. Reagents of Iodine (V). Some Further Reagents of Iodine (lll). Index of Compounds and Methods. Subject Index. Foreword. Preface. General Considerations: Introduction. A Note on Classes and Nomenclature. Bonding and Structure in Hypervalent Iodine. Reactivity Patterns. Practical Aspects. General References. Preparative Methods for Hypervalent Iodine Reagents: [Bis(acyloxy)iodo]arenes. (Difluoroiodo)- and (dichloroiodo)arenes. Iodosylarenes. [Hydroxy(iosyloxy)iodo]benzene and its Analogues. Reagents of Iodine (V). (Diacetoxyiodo)benzene: Acetoxylation. Transformations of Carbonyl Compounds. Phenolic Oxidation. Oxidation of Nitrogen Compounds. Hypervalent iodine Reagents in Combination with Azido Compounds. DIB and Sodium Azide in Combination with Other Reagents. Transformations of Alkynes Involving Thiophenols and Diphenyl Diselenide. Miscellaneous Reactions. [Bis(acyloxy)iodo]arenes: Part A: Reactions with [bis(trifluoroacetoxy)iodo]benzene. Transformations of Alkynes. Transformations of Ketones. Phenolic Oxidation. Oxidation of Nitrogen Compounds. Transfomration of Sulfur Compounds. Miscellaneous Transformations. Part B: Reactions with [bis(acyloxy)iodo]arenes. Oxidations. Homolytic Alkylation and Arylation. Iodosylbenzene: Reactions with Unsaturated Compounds. Reactions with Alcohols and Carbonyl Compounds. Reactions with NitrogenCompounds. Reactions with Sulfur and Other Compounds. (Difluoroiodo)-and (dichloroiodo)arenes: Chlorination. Remote Functionalism, of Steroids. Fluorination. Further Transformations. <


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@qu:"I suspect there will be no synthetic chemist who, after reading this book, will not try to include the valuable hypervalent iodine reagents in their synthetic plans." @source:--Andrew N. Boa in CHEMISTRY IN BRITAIN