Some New Radical Reactions of Xanthates

Xanthates are convenient precursors of a variety of radicals that can be captured in an inter- or intramolecular fashion. Overall, the process involves rupture of the sulfide C-S bond and addition of the elements of the xanthate to the olefinic trap. The xanthate in the product can be used in another radical sequence or ionically modified in a great variety of ways. S-Propargyl xanthates exhibit a special but interesting behaviour which involves a sigmatropic rearrangement to the corresponding allene and ring closure to a novel betaine.