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.
D. H. R. Barton, R. S. H. Motherwell and W. B. Motherwell, J. Chem. Soc., Perkin Trans. 1, 1981, 2363 DOI: 10.1039/P19810002363
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