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Concerning Amines - 1st Edition - ISBN: 9780080119137, 9781483185903

Concerning Amines

1st Edition

Their Properties, Preparation and Reactions

Author: David Ginsburg
Editor: Robert Robinson
eBook ISBN: 9781483185903
Imprint: Pergamon
Published Date: 1st January 1967
Page Count: 208
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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


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



No. of pages:
© Pergamon 1967
1st January 1967
eBook ISBN:

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

Ratings and Reviews