The racemization of an optically active sulfilimine and optically active aminosulfonium salts

The racemization of an optically active sulfilimine and optically active aminosulfonium salts was kinetically measured. The mechanism of the racemization of optically active sulfilimine (?)-1 has been established. The activation parameters for the racemization of (?)-1 and (?)-7 were calculated. A plausible pathway for the decomposition of (?)-6, (?)-7 and (?)-8 with tetra-n-butylammonium bromide in the presence of methyl ethyl ketone to provide 3-p-tolylthio-2-butanone 22 is proposed.