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Grignard Reactions

  1. Philip E. Rakita

Published Online: 14 JAN 2005

DOI: 10.1002/0471238961.0718090719091222.a01.pub2

Kirk-Othmer Encyclopedia of Chemical Technology

Kirk-Othmer Encyclopedia of Chemical Technology

How to Cite

Rakita, P. E. 2005. Grignard Reactions. Kirk-Othmer Encyclopedia of Chemical Technology. .

Author Information

  1. Armour Associates, Ltd.

Publication History

  1. Published Online: 14 JAN 2005

Abstract

The term Grignard reaction refers to both the preparation of a class of organomagnesium halide compounds and their subsequent reaction with a wide variety of organic and inorganic substrates.

The general sequence of the reactions is now embodied in the following generic forms, where RX = an organic halide (most typically a chloride or bromide, although fluorides can be induced to react); S = a coordinating solvent (such as an ether or an amine); and AZ = a substrate with an electronegative group, Z: RX + Mg + n S [RIGHTWARDS ARROW] RMgX·Sn RMgX·Sn + AZ [RIGHTWARDS ARROW] RAZMgX·Sn RAZMgX·Sn[RIGHTWARDS ARROW] RA + ZMgX·Sn.

The development of improved industrial procedures, including the substitution of tetrahydrofuran (THF) for diethyl ether and the demonstration that the less reactive, but significantly less expensive, vinyl and aryl chlorides could be successfully used, has greatly expanded the commercial possibilities of this reaction. In the flavor, fragrance, pharmaceutical, and fine chemical industries, its use can generally be regarded as routine.

The great value of the Grignard reaction to the synthetic chemist is its general applicability as a building block for an impressive range of structures and functional groups.

Keywords:

  • grignard reactions;
  • magnesium preparation;
  • solvent;
  • organohalogen component;
  • industrial process;
  • analysis;
  • fire hazards;
  • regulations;
  • bases;
  • asymmetric syntheses;
  • catalyst;
  • Ziegler–Natta process;
  • methacrylates;
  • inorganic chlorides