Journal of the Chemical Society. Perkin transactions I p. 2363 - 2367 (1981)
Update date:2022-08-04
Topics: Experimental terms Epoxides Radical-induced ring opening Wharton rearrangement Convenient alternative
Barton, Derek H. R.
Motherwell, Robyn S. Hay
Motherwell, William B.
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.
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