Radical-induced ring opening of epoxides. A convenient alternative to the wharton rearrangement
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2363-2367
- https://doi.org/10.1039/p19810002363
Abstract
Tri-n-butyltin hydride reduction of an αβ-epoxy-O-thiocarbonylimidazolide derivative of an alcohol leads via oxiran ring-opening to the formation of an allylic alkoxyl radical. By a suitable choice of experimental conditions, this radical can either be quenched by hydrogen-atom transfer from the stannane or allowed to undergo further rearrangement.Keywords
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