Some aspects of the radical chemistry of xanthates

Xanthates and related thiocarbonylthio derivatives have proved to be exceedingly useful substrates for both inter- and intra- molecular radical additions. The intermolecular addition to unactivated alkenes, in particular, provides tremendous opportunities for synthesis: various functional groups can be brought together under mild, neutral conditions. Since the adduct is also a xanthate, iteration allows the formation of block polymers through a controlled radical polymerisation (the RAFT/MADIX technology). Also of some importance is the access to highly substituted aromatic and heteroaromatic derivatives.