Diazo Compounds

Diazo Compounds

Properties and Synthesis

1st Edition - January 15, 1987

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  • Author: Manfred Regitz
  • eBook ISBN: 9780323144728

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Diazo Compounds: Properties and Synthesis focuses on the properties and syntheses of aliphatic diazo compounds. This monograph explores the application of diazo compounds in organic synthesis. Organized into two parts encompassing 16 chapters, this book starts with an overview of the structurally inherent effects of diazoalkenes. This monograph then examines the most important contribution of diazo compounds to the chemistry of carbenes and cycloadditions. Other chapters deal with structure, thermal behavior, acidic decomposition, spectroscopic properties, photochemistry of diazoalkenes, and synthetic methods. This book further discusses the qualitative and quantitative studies of the thermal stabilities of alkyl and aryl diazomethanes. The final chapter deals with the isotope-labeled diazo compounds that are of great importance for investigations of organic reaction mechanisms. This book is intended for chemists with an interest in the synthetic application of diazo compounds. Students and researchers engaged in the study of the physical properties of diazo compounds will find this book extremely useful.

Table of Contents

  • Preface

    Part I Properties of Aliphatic Diazo Compounds

    Chapter 1 Structure and Spectroscopic Properties

    1.1 The Constitution of Diazoalkanes

    1.2 Structure and Bonding of Diazoalkanes

    1.3 Cis-Trans Isomerism of the α-Diazocarbonyl Compounds

    1.4 Metal Complexes with Diazo Compounds as Ligands

    1.5 Spectroscopic Properties of Diazoalkanes


    Chapter 2 Thermal Properties

    2.1 Introduction

    2.2 Alkyl and Aryl Diazomethanes

    2.3 α-Diazocarbonyl Compounds

    2.4 α-Diazophosphoryl Compounds


    Chapter 3 Reactivity toward Acids

    3.1 The Acid-Stability of Diazoalkanes

    3.2 C- and N-Protonation

    3.3 Kinetics and Mechanism of the Reactions with Acids

    3.4 Influence of Solvent on Kinetics and Product Distribution

    3.5 Products of the Acid-Catalyzed Decomposition

    3.6 Diazocarbonyl Compounds and Lewis Acids


    Chapter 4 Photochemistry of Aliphatic Diazo Compounds

    4.1 Introduction

    4.2 Diazoalkane-Diazirine Isomerization

    4.3 Generation of Carbenes from Diazo Compounds

    4.4 Wolff Rearrangement


    Part II Syntheses of Aliphatic Diazo Compounds

    Chapter 5 Diazotization of Amines

    5.1 Introduction

    5.2 Diazoalkanes

    5.3 Fluoro- and Cyanodiazoalkanes

    5.4 Diazocarbonyl Compounds

    5.5 α-Diazophosphoryl Compounds

    5.6 Diazoazoles


    Chapter 6 The Forster Reaction

    6.1 Introduction

    6.2 Diazomethane and Aryldiazomethanes

    6.3 α-Diazoketones and Sulfones


    Chapter 7 Introduction of the Diazo Group by Nitrosation

    7.1 Introduction

    7.2 Diazoazoles

    7.3 Diazocarbonyl Compounds


    Chapter 8 Dehydrogenation of Hydrazones

    8.1 Introduction

    8.2 Mercury(II) Oxide

    8.3 Silver Oxide

    8.4 Manganese(IV) Oxide

    8.5 Lead(IV) Acetate

    8.6 Iodine

    8.7 Miscellaneous


    Chapter 9 The Bamford-Stevens Reaction

    9.1 Introduction

    9.2 Aryl- and Alkyldiazoalkanes

    9.3 Metallated Diazoalkanes

    9.4 α, β-Unsaturated Diazoalkanes

    9.5 α-Diazocarbonyl Compounds

    9.6 α-Diazophosphoryl Compounds


    Chapter 10 Alkaline Cleavage of β-(Ν-Alkyl-N-nitrosoamino)ketones and -sulfones

    10.1 Introduction


    Chapter 11 Alkaline Cleavage of (N-Alkyl-N-nitroso-aminomethyl)carboxamides and -urethanes


    Chapter 12 Acyl Cleavage of N-Alkyl-N-nitrosoacidamides

    12.1 Introduction

    12.2 Mechanism of Cleavage

    12.3 N-Alkyl-N-nitrosourethanes

    12.4 N-Alkyl-N-nitrosoureas

    12.5 N-Alkyl-N'-nitro-N-nitrosoguanidines

    12.6 N-Alkyl-N-nitrosocarboxamides

    12.7 N-Alkyl-N-nitroso-p-toluenesulfonamides


    Chapter 13 Diazo Group Transfer

    13.1 Introduction

    13.2 To Active Methylene Compounds

    13.3 To α-Acylcarbonyl Compounds

    13.4 Diazo Group Transfer to Alkenes

    13.5 Diazo Group Transfer to Acceptor-Substituted Methylene Triphenylphosphoranes and Triphenylphosphonium Salts

    13.6 Diazo Group Transfer to Alkynes


    Chapter 14 Substitution Reactions of Diazoalkanes

    14.1 Introduction

    14.2 Metallation

    14.3 Transmetallation Reactions

    14.4 Halogenation

    14.5 Nitration

    14.6 C-Alkylation

    14.7 C-Acylation

    14.8 Acyl Cleavage

    14.9 Miscellaneous Reactions


    Chapter 15 Miscellaneous Methods

    15.1 Ring Cleavage of Heterocycles

    15.2 Condensation Reactions

    15.3 Cleavage Reactions

    15.4 Fragmentation of Heterocyclic Compounds


    Chapter 16 Isotope-Labeled Diazo Compounds

    16.1 Introduction

    16.2 Diazomethanes

    16.3 α-Diazocarbonyl Compounds





Product details

  • No. of pages: 608
  • Language: English
  • Copyright: © Academic Press 1987
  • Published: January 15, 1987
  • Imprint: Academic Press
  • eBook ISBN: 9780323144728

About the Author

Manfred Regitz

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