On the mechanism of reductive degradation of dithiocarbonates by tributylstannane

Abstract

Product analysis of the reaction between O-isopropyl S-4-phenylbut-3-enyl dithiocarbonate and tributylstannane, initiated by azoisobutyronitrile in boiling benzene or toluene, indicates that the first step in the reductive degradation of dithiocarbonates by trialkylstannanes involves the homolytic attack of trialkyltin radical on the thioxo sulphur according to the Barton mechanism, rather than on the thio sulphur as displayed in a proposed alternative mechanism.