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On the Reduction of S-Alkyl-thionocarbonates (Xanthates) with Phosphorus Compounds

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journal contribution
posted on 15.04.2003, 00:00 by Jean Boivin, Rafik Jrad, Stéphanie Juge, Van Tai Nguyen
Reductive cleavage of the carbon−sulfur bond present in S-alkyl-thionocarbonates (xanthates) was achieved by high-yielding, tin-free radical reactions based on phosphorus reagents. The combination hypophosphorous acid/triethylamine/AIBN led to fast, efficient, and smooth formation of the alkane. Reduction with diethyl phosphite was sufficiently slow to permit sequential intermolecular addition of a 2-oxoalkyl xanthate onto an olefin followed by cleavage of the newly formed carbon−sulfur bond.