Abstract
Reactions of tetraphenylantimony mercaptides, Ph 4SbSC 6H 4Y, 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 transPhCHCHCH 2Br. In a competition reaction for ClCH 2SMe, Ph 4SbSC 6H 5 was shown to be only slightly (ca. 1.2 times) more reactive than Ph 4SbSC 6H 4OMe- p. The initial sulphur-containing product or reaction with p-toluenesulphonyl chloride, namely the thiosulphonate, p-MeC 6H 4SO 2SC 6H 4Y, reacts further with Ph 4SbSC 6H 4Y to produce the disulphide, (YC 6H 4S) 2. Benzoyl peroxide and Ph 4SbSC 6H 4Y provide PhSbOCOPh and disulphide.
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