We had reported that the reaction of disulfides with 2.5 equivalents of selectfluor (an electrophilic fluorinating reagent) efficiently produced the corresponding thiosulfonates in high yields accompanied with small amounts of sulfonyl fluorides. We also had found that sulfonyl fluorides could be effectively obtained from the reaction of disulfides with 6.5 equivalents of selectfluor. This time, the reactions of sulfides with electrophilic haloginating reagents, such as N-chlorosuccinimide (NCS) and N-bromosuccinimide (NBS), were examined to synthesize thiosulfonates or sulfonyl halides. Unfortunately, thiosulfonates could not selectively be obtained. The desired sulfonyl halides were effectively afforded from the reaction of disulfides with 6.0 equivalents of NCS or NBS in aqueous acetonitrile.
