Isonitrile Chemistry

Isonitrile Chemistry

1st Edition - January 28, 1971

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  • Editor: Ivar Ugi
  • eBook ISBN: 9780323157339

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Organic Chemistry, Volume 20: Isonitrile Chemistry discusses the fundamental aspects of the chemistry of isonitriles. This book provides an introduction to as well as a thorough coverage of isonitrile chemistry. Organized into 10 chapters, this volume begins with an overview of the general properties and structure of isonitriles. This text then examines the quantitative study of the kinetics of isonitrile rearrangement as well as the principal resonance structure of the isonitrile molecule. Other chapters consider the experimental and theoretical findings on the fall-off behavior of the unimolecular rate constants of different isonitriles with pressure. This book discusses as well the behavior of isonitriles toward a center of low electron density, which is particularly manifested in the reactivity of alkyl and aryl isonitriles toward diborane and alkyl or arylboranes. The final chapter deals with the inorganic coordination chemistry of isonitriles. This book is a valuable resource for organic chemists.

Table of Contents

  • List of Contributors


    1. The Structure of Isonitriles

    I. The History of the Structure of Isonitriles

    II. Some Physicochemical Consequences of the Structure of the Isocyano Group


    2. Isonitrile Syntheses

    I. Introduction

    II. The Dehydration of N-Monosubstituted Formamides and Related α-Eliminations

    III. The Classical Isonitrile Syntheses and Related Reactions

    IV. Miscellaneous Reactions by Which Isonitriles Are Formed


    3. Kinetics of the Isonitrile-Nitrile Rearrangement

    I. Introduction

    II. Thermal Rearrangement

    III. External Excitation


    4. Simple α-Additions

    I. Introduction

    II. α-Addition Reactions of Isonitriles with Reactive Hydrogen Compounds

    III. α-Addition Reactions of Isonitriles with Reactive Halogen Compounds

    IV. Oxidation of Isonitriles

    V. Reduction of Isonitriles

    VI. Reactions with Carbenes and Nitrenes

    VII. Reaction with Organometallic Compounds

    VIII. Radical Reactions of Isonitriles

    IX. Reactions Related to α-Additions


    5. Cyclization Reactions

    I. Introduction

    II. Four-Membered Rings

    III. Five-Membered Rings

    IV. Six-Membered Rings

    V. Seven-Membered Rings


    6. The Reaction of Isonitriles with Boranes

    I. Isonitrile-Organoborane Reactions

    II. Isonitrile-Organoaluminum and Cyanide-Organoaluminum Reactions

    III. Cyanide-Organoborane Reactions

    IV. Related Reactions: The Reaction of Carbon Monoxide and Other Lewis Bases with Organoboranes


    7. The Passerini Reaction and Related Reactions

    I. Introduction

    II. α-Acyloxycarbonamides

    III. The Mechanism of the Passerini Reaction

    IV. Tetrazoles

    V. α-Hydroxyamides

    VI. α,γ-Diketoamides


    8. Four-Component Condensations and Related Reactions

    I. Introduction and General Remarks

    II. Hydantoin-4-imides and 2-Thiohydantoin-4-imides

    III. Acylated α-Amino- and α-Hydrazinocarbonamides

    IV. Stereoselective Syntheses and the Reaction Mechanism of 4 C C

    V. β-Lactams and Penicillanic Acid Derivatives

    VI. Urethanes

    VII. The Bucherer-Bergs Reaction

    VIII. N-Alkyl-3-acyl-4-hydroquinoline-4-carbonamides

    IX. Diacylimides, Amides, Thioamides, Selenoamides, and Amidines of α-Amino Acids

    X. Tetrazoles


    9. Peptide Syntheses

    I. The General Concept

    II. The Present Status of Classical Methods

    III. Potential Advantages of the 4 C C Concept

    IV. Isonitrile and Amine Components—Model Reactions

    V. Tactics of the 4 C C Peptide Synthesis


    10. Coordinated Isonitriles

    I. Introduction

    II. Structure and Bonding in Isonitrile Complexes

    III. Reactions of Coordinated Isonitriles

    IV. The Synthesis of Metal Isonitrile Complexes


    Addendum Recent Developments in Isonitrile Chemistry

    Author Index

    Subject Index

Product details

  • No. of pages: 292
  • Language: English
  • Copyright: © Academic Press 1971
  • Published: January 28, 1971
  • Imprint: Academic Press
  • eBook ISBN: 9780323157339

About the Editor

Ivar Ugi

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  • HeinerEckert Sat Apr 27 2019

    Ivar Ugi, Isonitrile Chemistry

    I possess a copy of the original edition, a wonderful book on isocyanides. This issue is a felicitous second edition, overdue for a long time.