Concerning Amines

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

Biosynthesis

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

Basicity

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

Pyrroles

Fischer Indole Synthesis

Pyridines

Skraup Synthesis

Bischler-Napieralski Reaction

Enamines

Further Reactions of Carbonyl Compounds with Amines

The Eschweiler Reaction

The Vilsmeyer Reaction

The Von Braun Reaction

The Mannich Reaction

Index