Overview

The one-step organic synthesis with metals discovered by Barbier almost 100 years ago was widely applied with magnesium as the main metal until the end of the 1960s. In modern Barbier reactions, magnesium has been successfully replaced with lithium and zinc. More recently tin and aluminium have also been introduced together with other metals such as lead, manganese, cerium etc. Unexpected new developments, e.g., the use of aqueous solvents, are of great interest to synthetic chemists, especially those working with industrial processes increasingly controlled by ever-tighter environmental regulations. This book offers a completely new perspective on a simple synthetic method that has only been reviewed once before - by the same author some 15 years ago. Chapter one traces the development of reactions of metals with organohalides leading on to the Barbier reaction and finally to the Grignard reagent formation reaction. The second chapter deals with synthetic applications of the Barbier reaction. The following chapter discusses Barbier-type reactions with other metals. The fourth chapter is concerned with the detailed mechanism of the reaction. Finally, in the last chapter, technical details are presented which will enable practitioners to perform these one-step reactions smoothly and effectively.

Full Product Details

Author:   Cornelis Blomberg ,  Craig L. Blomberg
Publisher:   Springer-Verlag Berlin and Heidelberg GmbH & Co. KG
Imprint:   Springer-Verlag Berlin and Heidelberg GmbH & Co. K
Volume:   31
Weight:   0.430kg
ISBN:  

9783540571698

ISBN 10:   3540571698
Pages:   183
Publication Date:   16 December 1993
Audience:   College/higher education ,  Professional and scholarly ,  Postgraduate, Research & Scholarly ,  Professional & Vocational
Format:   Hardback
Publisher's Status:   Active
Availability:   Out of stock  
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Table of Contents

1 Introduction.- 1.1 Magnesium: A New Metal in Organic Synthesis.- 1.2 The Early History of Organozinc Chemistry.- 1.3 The Early History of Organomagnesium Chemistry.- 1.4 The Barbier Reaction.- 1.5 More Recent Developments in Barbier Chemistry.- 1.6 Contents of the Following Chapters.- 1.7 References.- 2 Synthetic Applications of the Barbier Reaction.- 2.1 Synthetic Procedures: One-Step or Two-Step?.- 2.2 The Replacement of Zinc by Magnesium in the Reformatsky Reaction.- 2.3 Barbier Reactions with Allylic Halides.- 2.4 Other Barbier Reactions.- 2.5 Conclusion.- 2.6 References.- 3 Barbier-Type Reactions with Other Metals.- 3.1 Introduction.- 3.2 Sodium in One-Step Processes.- 3.3 Lithium in Barbier-Type Reactions.- 3.4 Zinc in Barbier-Type Reactions.- 3.5 Other Metals in Barbier-Type Reactions.- 3.6 Summary.- 3.7 References.- 4 The Mechanism of the Barbier Reaction.- 4.1 Introduction.- 4.2 Mechanism of the Interaction of Metals with Organo Halides.- 4.3 Mechanism of the Grignard Reagent Formation Reaction.- 4.4 Mechanism of the Barbier Reaction.- 4.5 References.- 5 Experimental Procedures for Barbier Reactions.- 5.1 Introduction.- 5.2 Starting Heterogeneous Reactions with Metals.- 5.3 Reactions with Magnesium.- 5.4 Reactions with Lithium.- 5.5 Reactions with Zinc.- 5.6 References.

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