Reductive desulfurization using tributyltin hydride

Reaction of tributyltin hydride with a variety of organic sulfides gives results which depend on the structure of the starting material. Acyclic sulfides undergo desulfurization leading to hydrocarbons in varying yields. However, 2,5-dihydrothiophenes give dienes and 3,6-dihydro-2H-thiopyrans are inert.