The Barbier reaction and related one-step processes
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Bibliographic Information
The Barbier reaction and related one-step processes
（Reactivity and structure : concepts in organic chemistry, v. 31）
Springer-Verlag, c1993
- : gw
- : us
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Includes bibliographical references
Description and Table of Contents
Description
The significant increase in applications of Barbier and Barbier-type reactions in (in-) organic synthesis over the past twenty-five years, combined with repeated stimulation on the part of Springer-Verlag (Dr. R. Stumpe) were strong in centives for me to write this book. My earliest activities in this field include a modest and first-ever review article (in cooperation with Dr. F. A. Hartog who at that time (1977) did his doctoral research on the Barbier reaction). References to this review article, as mentioned in the Science Citation Index till recently are a good indication for a continued interest in this simple synthetic procedure. The subtitle of this monograph, Related One-Step Processes, may require the following clarification. A synthesis with the aid of an organometallic compound is usually carried out in two steps: 1) the organometallic reagent is prepared from an organo halide and a metal in a solvent, 2) a chosen substrate is added to this reagent. In a Barbier reaction these two steps are combined: a mixture of the organo halide and the substrate is added to a suspension of the metal-in an appropriate solvent.
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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