Regioselectivity and control in alkene formation from a carbonium ion after diphenylphosphinoyl migration
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 550-565
- https://doi.org/10.1039/p19770000550
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.Keywords
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