Newer Methods of Preparative Organic Chemistry V3 - 1st Edition - ISBN: 9780123956491, 9780323146104

Newer Methods of Preparative Organic Chemistry V3

1st Edition

Editors: Wilhelm Foerst
eBook ISBN: 9780323146104
Imprint: Academic Press
Published Date: 1st January 1964
Page Count: 558
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Description

Newer Methods of Preparative Organic Chemistry, Volume III focuses on the improved methods in preparative organic chemistry. This book presents a variety of topics, including the synthesis of acetylenes, methods for the preparation of pyrylium salts, and the use of phosphoric acid chlorides in the preparation of esters of phosphoric acids. Organized into 11 chapters, this volume starts with an overview of the reaction between methylene and sulfur involving dehydrogenation or oxidation. This text then examines the chemistry of pyridine, which exhibits different reaction characteristics than benzene. Other chapters consider the cyclic derivatives of carboxylic acids, such as lactams, lactones, or thiolactones, which can be converted by partial reduction into heterocycles of the same ring size. The final chapter outlines the fundamental reactions of diazoketones and discusses the preparative significance of the diazoketones. This book is a valuable resource for synthetic organic chemists involved in research institutions and industrial laboratories.

Table of Contents


Contributors to Volume III

Preface

Foreword

The Reactions of Sulfur with Araliphatic and Aliphatic Compounds

The Development of the Willgerodt Reaction

The Mechanism of the Willgerodt Reaction

Newer Views Regarding the Course of the Reaction

Trithiones

Action of Sulfur on Aliphatic Ketones in the Presence of Ammonia, under Mild Temperature Conditions (Asinger Reaction)

Action of Sulfur on Alkyl-Substituted Aromatic and Heterocyclic Compounds

Action of Sulfur on Other Compounds

Experimental Examples

References

The Introduction of Substituents into the Pyridine Ring

Behavior of Pyridine during Substitution Reactions

Syntheses Involving the Use of Organometallic Pyridine Compounds

Reactivity of Substituents in the Pyridine Ring

Methods of Preparation of 4-Substituted Pyridine Derivatives

The Use of Pyridine-N-Oxides in the Preparation of Substituted Pyridines

Appendix

Experimental

References

Carbonyl-Olefin Transformation Using Triphenylphosphinemethylenes. The Wittig Reaction

Introduction

Triphenylphosphinemethylenes

Mechanism of the Wittig Reaction

Other Reactions

General Experimental

Appendix

References

N-Bromosuccinimide, Its Properties and Reactions the Course of Substitution

Introduction

General Discussion

Survey of the Reactivity of N-Bromosuccinimide

Experimental

Appendix

References

The Acyllactone Rearrangement; A Method for the Preparation of Heterocyclic Ring Systems

Introduction

Preparative Methods

Special Reactions

Enol Content of the α-Acyllactones

Optical Measurements of α-Acyllactones, -thiolactones, and -lactams and Their Rearrangement Products

Ring-Opening Mechanism of the α-Acyl-δ-lactones

Mechanism of the Rearrangement

Limitations of the Rearrangement with Respect to the Ring Size and the Functional Groups

Application of the α-Acyllactone Rearrangement to Special Syntheses

Conclusion

Experimental

References

Syntheses with Acid Amides, Particularly Formamide

Introduction

Syntheses in the Purine and Pyrimidine Series

Acid Amides and o-Phenylenediamine

Formamide and Compounds Containing a —NH—CO— Grouping

Syntheses of Imidazoles

Syntheses of Oxazoles

Synthesis of Imidazoles and Oxazoles Using Formamidine

Syntheses of Pyrimidines

Acid Amides and Halogen Compounds

Formamide and Mannich-Type Compounds

Thioformamide and Halogen Compounds

Synthesis of Trisformylaminomethane

Reactions of Trisformylaminomethane

Synthesis of a Few s-Triazine Derivatives

Acid Amide-Acyl Chloride Adducts and Their Use in Synthesis

Gas-Phase Reactions with Formamide

Experimental

References

Organic Syntheses Using Chloramine

Amines from Chloramine and Organometallic Compounds

Unsymmetrically Substituted Hydrazines from Amines and Chloramine

O-Alkyl and O-Arylhydroxylamines from Chloramine and Alkoxides or Phenoxides

Reaction between Mercapto Compounds and Chloramine

Aldehyde Chlorimines

References

Preparation of Esters, Amides, and Anhydrides of Phosphoric Acid

Introduction

Use of Acid Chlorides. Classical Methods

Esters Containing Protected Groups

Selective Removal of Protecting Groups

Phosphonic Esters. Michaelis-Arbusov Reaction

Enol Phosphates. Perkow Reaction

Amides and Guanidides of Phosphoric Acid

Problems of the Pyrophosphate and Phosphoric Acid Diester Synthesis

Carbodiimide Method

Carbamyl Phosphates

Reactions of Amidophosphoric Acids

Keteneacylals of Phosphoric Acid

Imidoylphosphates, Trichloroacetonitrile Method

Imidazolides of Phosphoric Acid

Experimental

References

Aromatic Compounds from Pyrylium Salts

Introduction

Conversion of Pyrylium Salts into Heterocyclic Compounds Possessing Aromatic Character

Conversion of Pyrylium Salts into Benzene Derivatives

Conversion of Pyrylium Salts into Azulene Derivatives

The Reaction Mechanism

Methods of Preparation of Pyrylium Salts

Experimental

References

The Formation of the Acetylenic Bond

Introduction

The Dehydrohalogenation of Dihalides or Haloalkenes

Dehalogenation and Reductive Dehalogenation Using Metals

Decomposition of Nitrogen-Containing Compounds

Miscellaneous Methods

By the Pyrolysis of Hydrocarbons and other Compounds

Experimental

References

Syntheses Using Diazoketones

Introduction

Mode of Reaction of Diazoketones

Preparation of Diazoketones

Syntheses Using Diazoketones

References

Author Index

Subject Index

Details

No. of pages:
558
Language:
English
Copyright:
© Academic Press 1964
Published:
Imprint:
Academic Press
eBook ISBN:
9780323146104

About the Editor

Wilhelm Foerst