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.

Document Type

Article

DOI

https://doi.org/10.1039/p19880001517

Publication Date

1-1-1988

Journal Title

Journal of the Chemical Society, Perkin Transactions 1

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