Issue 5, 1977

Regioselectivity and control in alkene formation from a carbonium ion after diphenylphosphinoyl migration

Abstract

Conversion of 2-hydroxyalkyldiphenylphosphine oxides into allylphosphine oxides by acid-catalysed diphenyl-phosphinoyl migration shows complete regioselectivity in favour of the more substituted olefin when the migration origin is unsymmetrical. The other, less substituted olefin is formed exclusively when a trimethylsilyl group is present on the appropriate carbon atom as it both increases the rate of the rearrangement and is lost in preference to a proton. The allylphosphine oxides are used in diene synthesis.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1977, 550-565

Regioselectivity and control in alkene formation from a carbonium ion after diphenylphosphinoyl migration

A. H. Davidson, I. Fleming, J. I. Grayson, A. Pearce, R. L. Snowden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1977, 550 DOI: 10.1039/P19770000550

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