McCormack reaction

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

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

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[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.