Concerning Amines

Concerning Amines

Their Properties, Preparation and Reactions

1st Edition - January 1, 1967

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  • Author: David Ginsburg
  • eBook ISBN: 9781483185903

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Concerning Amines: Their Properties, Preparation and Reactions attempts to describe the accumulated knowledge on the properties of amines. This text first discusses nitrogen atom contained in amines, along with the basicity, geometry, nomenclature, occurrence, reaction, and preparation of these derivatives of ammonia. This book then explains the stereochemistry of the amino group and of quaternary ammonium compounds. Amine salts; absolute configuration of asymmetric amines; and influence of amino group are also tackled. This text also looks into the amino group in heterocyclic aromatic systems. This book concludes by explaining the syntheses of heterocyclic amines, enamines, and further reactions of carbonyl compounds with amines, including the Eschweiler, Vilsmeyer, and von Braun reactions. This publication will be invaluable to those interested in studying the properties of amines, such as chemists and students of chemistry.

Table of Contents

  • Preface

    Editorial Preface

    The Nitrogen Atom

    Types of Amines

    Basicity of Amines

    Geometry of Amines and Ammonium Compounds

    Nomenclature of Amines

    Physical Properties of Amines

    Occurrence of Amines in Nature

    Preparation of Amines

    Laboratory and Industrial Synthesis


    Practical Considerations in Preparation of Amines

    Reduction of Nitro Compounds

    Alkylation of Ammonia

    Alkylation of the Phthalimide Anion (Gabriel Synthesis)

    Reductive Alkylation

    The Leuckart Reaction

    The Ritter Reaction

    Reduction of Oximes

    Reduction of Cyanides

    Various Rearrangements Leading to Amines

    The Hofmann Reaction

    The Curtius Reaction

    The Schmidt Reaction

    The Lossen Rearrangement

    Summary of Preparative Methods

    Reactions of Amines


    Alkylation of Amines

    Cyclic Immonium Intermediates

    Formation of Quaternary Ammonium Salts

    Formation of Quaternary Ammonium Hydroxides

    The Hofmann Exhaustive Methylation and Degradation Reaction

    Oxidation of Amines

    Acylation of Amines

    The Hinsberg Reaction

    Reaction of Amines with Nitrous Acid

    Aliphatic Amines

    Primary Aromatic Amines—Diazonium Salts

    The Sandmeyer Reaction

    Action of Iodide Ion on Diazonium Salts

    The Schiemann Reaction

    Replacement of Diazonium Group by Hydroxyl

    Replacement of Diazonium Group by Alkoxyl

    Reduction of Diazonium Salts

    Coupling Reaction

    Secondary and Tertiary Amines

    Stereochemistry of the Amino Group

    Stereochemistry of Quaternary Ammonium Compounds

    Amine Salts—Resolution of Racemates of Asymmetric Carbon Compounds

    Absolute Configuration of Asymmetric Amines

    Directive Influence of Amino Group in Electrophilic Aromatic Substitution

    Nitration of Aromatic Amines

    Sulphonation of Aromatic Amines

    The Sulphonamides

    Halogenation of Aromatic Amines

    Preparation of Aromatic Amines via a Benzyne Intermediate

    Preparation of Diphenylamine and Triphenylamine

    Rearrangements Producing Aromatic Amino Derivatives

    The Amino Group in Heterocyclic Aromatic Systems

    Syntheses of Heterocyclic Amines


    Fischer Indole Synthesis


    Skraup Synthesis

    Bischler-Napieralski Reaction


    Further Reactions of Carbonyl Compounds with Amines

    The Eschweiler Reaction

    The Vilsmeyer Reaction

    The Von Braun Reaction

    The Mannich Reaction


Product details

  • No. of pages: 208
  • Language: English
  • Copyright: © Pergamon 1967
  • Published: January 1, 1967
  • Imprint: Pergamon
  • eBook ISBN: 9781483185903

About the Author

David Ginsburg

Affiliations and Expertise

James V Neel Distinguished University Professor, Departments of Internal Medicine, Pediatrics, and Communicable Diseases, and Human Genetics, Investigator, Howard Hughes Medical Institute, University of Michigan Medical School, Ann Arbor, Michigan

About the Editor

Robert Robinson

Affiliations and Expertise

Recently retired from editorship of Canadian Security magazine

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