Reactions of tetraphenylantimony mercaptides

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 or reaction with p-toluenesulphonyl chloride, namely the thiosulphonate, p-MeC₆H₄SO₂SC₆H₄Y, reacts further with Ph₄SbSC₆H₄Y to produce the disulphide, (YC₆H₄S)₂. Benzoyl peroxide and Ph₄SbSC₆H₄Y provide PhSbOCOPh and disulphide.