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McCormack reaction

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The McCormack reaction is a method for the synthesis of organophosphorus compounds. In this reaction a 1,3-diene and a source of R2P+ are combined to give phospholenium cation. The reaction is named after W. B. McCormack, a research chemist at duPont.

An illustrative reaction involves phenyldichlorophosphine and isoprene:[1]

The reaction proceeds via a pericyclic [2+4]-process. The resulting derivatives can be hydrolyzed to give the phosphine oxide. Dehydrohalogenation gives the phosphole.[2]

References

  1. ^ W. B. McCormack (1973). "3-Methyl-1-Phenylphospholene oxide". Organic Syntheses; Collected Volumes, vol. 5, p. 787.
  2. ^ Handbook of organophosphorus chemistry by Robert Engel, CRC Press, 1992. ISBN 0-8247-8733-1.
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