Newer Methods of Preparative Organic Chemistry V2

Contributors to Volume II

Preface

Foreword

Contents of Volume III

Syntheses with Acetoacetaldehyde

Acetoacetaldehyde

Synthesis of Derivatives

Syntheses in the Aliphatic Series

Ring-Closure Syntheses

Reaction of Intermediates

References

Preparation of Peptides and Ureas Using Reactive Amides or Imides

Introduction

Synthesis Through Carbonic Acid Imides (Isocyanate Method)

Synthesis with Imides and Amides of P3+ and P5+ Acids (Phosphorazo- and Phosphite Ester Methods)

Supplement

Summary

References

The Preparation of Long-Chain Carboxylic Acids from 1,3-Cyclohexanediones

Introduction

Methods

Preparation of Straight-Chain Monocarboxylic Acids

Preparation of Dicarboxylic Acids

Preparation of Branched-Chain Mono-, Di-, and Polycarboxylic Acids

Preparation of Hydroxy and Amino Acids

Ring Opening of Monosubstituted 1,3-Cyclohexanediones with Nitrous Acid and with Aryldiazonium Salts

Methods of H. Lettrè and A. Jahn

Experimental Examples

References

Ethyl 2-Cyclopentanonecarboxylate and Its Importance in Syntheses

Preparation

Physical Properties

Enol

Condensation with Halides

Cleavage to Ketones and Acids

Reduction

Cyanohydrins

The Grignard and Reformatsky Reactions

Enol Hydroxyl Exchange with Halogen

Replacement of the Carbonyl Oxygen by Sulfur

Condensation with Amines

Condensation with Phenols

Direct Condensations

Reaction at Carbon-3

Experimental Examples

Prospect

References

Ketene in Preparative Organic Chemistry

Introduction

General Properties

Reactions

Examples of Experiments

References

Preparative and Analytical Importance of Phosphines and Related Compounds

Preparation of Quaternary Compounds

Phosphines as Selective Reducing Agents

Derivatives of Tertiary Phosphines of Apparent Higher Valence

The Reactivity of Tertiary Arsines (also Stibine and Bismuthine)

Preparation of Phosphines

Procedures

References

Reduction of Carbonyl Compounds with Complex Hydrides

Theoretical Interpretation

Examples

Supplement

References

Alkylation of Aromatic Amines

Ring Alkylation of Aromatic Amines

Alkylation of Nitrogen Heterocycles

N-Alkylation of Aromatic Amines

Reaction Mechanisms

Summary

References

Chemical Synthesis of Intermediates of Carbohydrate Metabolism

Glucose-6-Phosphate

D-Glyceraldehyde-3-Phosphate

Dihydroxyacetone Phosphate

Hydroxypyruvic Acid Phosphate

L(—)α-Glycerophosphate

D-Glyceric Acid-2-Phosphate (2-Phosphoglyceric Acid)

D-Glyceric Acid-3-Phosphate (3-Phosphoglyceric Acid)

Phosphoenol Pyruvic Acid (Phosphoryl-enol Pyruvic Acid)

D-Erythrose-4-Phosphate

References

Amidomethylation

Definition and Importance of Amidomethylation

Amidomethylation with N-Hydroxymethylamides

Amidomethylation with N-Halomethylcarboxamides

Amidomethylation with N-Dialkylaminomethylcarboxamides and Their Quaternary Salts

Summary and Outlook

Experimental

References

Selective Catalytic Oxidations with Noble Metal Catalysts

General Statements

Oxidation of Primary Hydroxyl Groups

Oxidation of Secondary Hydroxyl Groups

Procedures

References

Alkylation of Phenols with Alkenes

Introduction

Ethylation of Phenols

Propylation of Phenols

Alkylations with Butylene and Isobutylene

Alkylation with Higher and Cyclic Alkenes

Properties of o-Alkyl Substituted Phenols

Mechanism of Reaction

Summary

References

Continuous Preparation of Phenylsodium

Examples

References

Newer Investigations on Oxidation with Lead Tetraacetate

Reactions with Hydroxyl Compounds

Reactions with CH Groups

Reaction at the Carbon-Carbon Double Bond

Reactions with Mercury Compounds

Investigations with Thallium (III) Acetate

Formation of Esters of Glycolic Acid and of Glyoxylic Acid

Formation of Lactones from Alkenes

Concluding Remarks

Supplement

Selected Preparations

References

Author Index

Subject Index