Hypervalent Iodine in Organic Synthesis

Series Editor:

  • O. Meth-Cohn, University of Sunderland, UK
  • Alan Katritzky, University of Florida, Gainesville, USA
  • C. Rees, Imperial College of Science and Technology, London, UK


  • A. Varvoglis, Aristotelian University of Thessaloniki

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


Book information

  • Published: November 1996
  • ISBN: 978-0-12-714975-2


"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."

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. [Hydroxy(tosyloxy)iodo]benzene and Its Analogues: Reactionswith Alkenes and Allenes. Reactions with Alkynes and Alcohols. Reactions with Keto Compounds. Reactions with Nitrogen, Sulfur, and Other compounds. Diaryliodonium Salts: Preparative Methods. Carbon-Carbon Bond-Forming Reactions. Arylation of Heteroatoms. Phenyliodonium Salts with an Aliphatic Moiety: Preparative Methods. Reactivity of Perfluoroalkyl Phenyliodonium Salts. Reactivity of Other Iodonium Salts. Phenyliodonium Zwitterions: Preparation. Reactivity of Iodine-Carbon Ylides. Reactivity of Iodine-Nitrogen Ylides. Reactivity of 1,4-dipoles. Reagents of Iodine)V_: Reactions with Iodylarenes. Reactions with Dess-Martin Reagent and o-iodylbenzoic Acid. Some Further Reagents of Iodine (III): o-Iodosylbenzoic Acid and Its Derivatives. Reagents with Iodine-Oxygen Bonds. Reagents with Iodine-Nitrogen Bonds. Index of Compounds and Methods. Subject Index.