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The Halogen-Metal Interconversion Reaction with Organolithium Compounds

  1. Reuben G. Jones1,
  2. Henry Gilman2

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or006.07

Organic Reactions

Organic Reactions

How to Cite

Jones, R. G. and Gilman, H. 2011. The Halogen-Metal Interconversion Reaction with Organolithium Compounds. Organic Reactions. 6:7:339–366.

Author Information

  1. 1

    Eli Lilly and Company

  2. 2

    Iowa State College

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The reaction of an organic halide with an organometallic compound in which the metal and the halogen atoms exchange laces is known as the halogen-metal interconversion reaction. Numerous studies have established the fact that the halogen-lithium interconversion is a general and widely applicable reaction. Many organic halides do not react satisfactorily with metallic lithium to form RLi compounds or with metallic magnesium to form Grignard reagents. However, the desired organolithium compound often can be obtained by a halogen-metal Interconversion reaction. The halogen-metal interconversion greatly extends the utility of organolithium and Grignard-type reactions.

Keywords:

  • halogen-metal interconversion;
  • organolithium compounds;
  • halogen atoms;
  • side reactions;
  • Grignard reactions