REACTIONS OF TETRAPHENYLANTIMONY MERCAPTIDES

Article abstract of DOI:10.1016/S0022-328X(00)82449-3

Reactions of tetraphenylantimony mercaptides, Ph4SbSC6H4Y, with electrophilic species in chlorocarbon solutions are reported.With chloromethyl methyl sulphide, allyl halides, sulphenyl halide, acyl halides, halogens, and triphenyltin chloride, ready and complete halide-mercaptide exchanges occur.No allylic rearrangement is found in the reaction with trans-PhCH=CHCH2Br.In a competition reaction for ClCH2SMe, Ph4SbSC6H5 was shown to be only slightly (ca. 1.2 times) more reactive than Ph4SbSC6H4OMe-p.The initial sulphur-containing product of reaction with p-toluenesulphonyl chloride, namely the thiosulphonate, p-MeC6H4SO2SC6H4Y, reacts further with Ph4SbSC6H4Y to produce the disulphide, (YC6H4S)2.Benzoyl peroxide and Ph4SbSC6H4 provide PhSbOCOPh and disulphide.