Hypervalent Iodine Chemistry E-Book

Viktor V. Zhdankin

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 754

Veröffentlichungsjahr: 2013

Beschreibung

Hypervalent Iodine Chemistry is the first comprehensive text covering all of the main aspects of the chemistry of organic and inorganic polyvalent iodine compounds, including applications in chemical research, medicine, and industry.

Providing a comprehensive overview of the preparation, properties, and synthetic applications of this important class of reagents, the text is presented in the following way: 

• The introductory chapter provides a historical background and describes the general classification of iodine compounds, nomenclature, hypervalent bonding, structural features, and the principles of reactivity of polyvalent iodine compounds.
• Chapter 2 gives a detailed description of the preparative methods and structural features of all known classes of organic and inorganic derivatives of polyvalent iodine.
• Chapter 3, the key chapter of the book, deals with the many applications of hypervalent iodine reagents in organic synthesis.
• Chapter 4 describes the most recent achievements in hypervalent iodine catalysis.
• Chapter 5 deals with recyclable polymer-supported and nonpolymeric hypervalent iodine reagents.
• Chapter 6 covers the "green" reactions of hypervalent iodine reagents under solvent-free conditions or in aqueous solutions.
• The final chapter provides an overview of the important practical applications of polyvalent iodine compounds in medicine and industry.

This book is aimed at all chemists interested in iodine compounds, including academic and industrial researchers in inorganic, organic, physical, medicinal, and biological chemistry. It will be particularly useful to synthetic organic and inorganic chemists, including graduate and advanced undergraduate students. It comprehensively covers the green chemistry aspects of hypervalent iodine chemistry, making it especially useful for industrial chemists.

Leseprobe

Contents

Cover

Title Page

Copyright

Preface

Chapter 1: Introduction and General Overview of Polyvalent Iodine Compounds

1.1 Introduction

1.2 Classification and Nomenclature of Polyvalent Iodine Compounds

1.3 Hypervalent Bonding

1.4 General Structural Features

1.5 General Principles of Reactivity

References

Chapter 2: Preparation, Structure and Properties of Polyvalent Iodine Compounds

2.1 Iodine(III) Compounds

2.2 Iodine(V) Compounds

2.3 Iodine(VII) Compounds

References

Chapter 3: Hypervalent Iodine Reagents in Organic Synthesis

3.1 Reactions of Iodine(III) Compounds

3.2 Synthetic Applications of Iodine(V) Compounds

3.3 Synthetic Applications of Iodine(VII) Compounds

References

Chapter 4: Hypervalent Iodine Catalysis

4.1 Catalytic Cycles Based on Iodine(III) Species

4.2 Catalytic Cycles Based on Iodine(V) Species

4.3 Tandem Catalytic Systems Involving Hypervalent Iodine and other Co-catalysts

4.4 Catalytic Cycles Involving Iodide Anion or Elemental Iodine as Pre-catalysts

References

Chapter 5: Recyclable Hypervalent Iodine Reagents

5.1 Polymer-Supported Iodine(III) Reagents

5.2 Polymer-Supported Iodine(V) Reagents

5.3 Recyclable Nonpolymeric Hypervalent Iodine(III) Reagents

5.4 Recyclable Nonpolymeric Hypervalent Iodine(V) Reagents

5.5 Recyclable Iodine Catalytic Systems

References

Chapter 6: Reactions of Hypervalent Iodine Reagents in Green Solvents and under Solvent-Free Conditions

6.1 Reactions of Hypervalent Iodine Reagents in Water

6.2 Reactions of Hypervalent Iodine Reagents in Recyclable Organic Solvents

6.3 Reactions of Hypervalent Iodine Reagents under Solvent-Free Conditions

References

Chapter 7: Practical Applications of Polyvalent Iodine Compounds

7.1 Applications of Inorganic Polyvalent Iodine Derivatives

7.2 Applications of Hypervalent Iodine(III) Compounds as Polymerization Initiators

7.3 Application of Iodonium Salts for Fluoridation in Positron Emission Tomography (PET)

7.4 Biological Activity of Polyvalent Iodine Compounds

References

Index

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Library of Congress Cataloging-in-Publication Data

Zhdankin, Viktor V., 1956–  Hypervalent iodine chemistry : preparation, structure and synthetic applications of polyvalent iodine

compounds / Viktor V. Zhdankin.   pages cm  Includes index.  ISBN 978-1-118-34103-2 (cloth) 1. Iodine compounds. 2. Organoiodine compounds. 3. Hypervalence (Theoretical chemistry)  I. Title.  QD181.I1Z43 2014  546′.7342–dc23 2013020439

A catalogue record for this book is available from the British Library.

ISBN: 9781118341032

Preface

Iodine is the heaviest non-radioactive element in the Periodic Table that is classified as a nonmetal and it is the largest, the least electronegative and the most polarizable of the halogens. It formally belongs to the main group p-block elements; however, the bonding description, structural features and reactivity of iodine compounds differ from the light main-group elements. The electronic structure of polyvalent iodine is best explained by the hypervalent model of bonding and, therefore, in modern literature organic compounds of trivalent and pentavalent iodine are commonly named as hypervalent iodine compounds. The reactivity pattern of hypervalent iodine in many aspects is similar that of transition metals – the reactions of hypervalent iodine reagents are commonly discussed in terms of oxidative addition, ligand exchange, reductive elimination and ligand coupling, which are typical of transition metal chemistry.

Since the beginning of the twenty-first century, the organic chemistry of hypervalent iodine compounds has experienced an unprecedented, explosive development. Hypervalent iodine reagents are now commonly used in organic synthesis as efficient multipurpose reagents whose chemical properties are similar to derivatives of mercury, thallium, lead, osmium, chromium and other metals, but without the toxicity and environmental problems of these heavy metal congeners. One of the most impressive recent achievements in the field of iodine chemistry has been the discovery of hypervalent iodine catalysis.

This book is the first comprehensive monograph covering all main aspects of the chemistry of organic and inorganic polyvalent iodine compounds, including applications in chemical research, medicine and industry. The introductory chapter (Chapter 1) provides a historical background and describes the general classification of iodine compounds, nomenclature, hypervalent bonding, general structural features and general principles of reactivity of polyvalent iodine compounds. Chapter 2 gives a detailed description of the preparative methods and structural features of all known classes of organic and inorganic derivatives of polyvalent iodine. Chapter 3, the central chapter of the book, deals with the applications of hypervalent iodine reagents in organic synthesis. Chapter 4 describes the most recent achievements in hypervalent iodine catalysis. Chapter 5 deals with recyclable polymer-supported and nonpolymeric hypervalent iodine reagents. Chapter 6 covers the “green” reactions of hypervalent iodine reagents, including solvent-free reactions, reactions in water and reactions in ionic liquids. The final chapter (Chapter 7) provides an overview of important practical applications of polyvalent iodine compounds in medicine and in industry.

This book is aimed at all chemists interested in iodine compounds, including academic and industrial researchers in inorganic, organic, physical, medicinal and biological chemistry. It will be particularly useful to synthetic organic and inorganic chemists, including graduate and advanced undergraduate students. The book also covers the green chemistry aspects of hypervalent iodine chemistry, including the use of water as solvent, reactions under solvent-free conditions, recyclable reagents and solvents and catalytic reactions, which makes it especially useful for industrial chemists. The last chapter provides a detailed summary of practical applications of polyvalent iodine compounds, including various industrial applications, biological activity and applications of iodonium salts in PET (positron emission tomography) diagnostics; this chapter should be especially useful for medical and pharmaceutical researchers. Overall, the book is aimed at a broad, multidisciplinary readership and specialists working in different areas of chemistry, pharmaceutical and medical sciences and industry.