ON THE MECHANISM OF THE DEOXYGENATION OF SECONDARY ALCOHOLS BY THE REDUCTION OF THEIR METHYL XANTHATES BY TIN HYDRIDES

Article abstract of DOI:10.1016/S0040-4020(01)90614-3

Two alternate proposals for the mechanism of reduction of xanthates by tributylstannane have been examined.Evidence has been secured that under normal reduction conditions the thiocarbonyl group is attacked reversibly.At a high enough temperature the carbon radical fragments to give eventually the reduction product.Under modified conditions, where no reducing agent (Sn-H) is present, the radical formed eliminates methylthiotributylstanne and affords the thiocarbonyloxy radical observed in the e.s.r. spectrum.