Rearrangement of radicals with migration of the chlorine atom from sulfur to carbon during the reaction of thiols with vinylsulfonyl chloride

Article abstract of DOI:10.1007/BF00923221

1. A study was made of the reaction of n-butanethiol and thiophenol with vinylsulfonyl chloride at ～20° in an argon atmosphere. The reaction products are, respectively, β-chloroethyl butyl sulfide and β-chloroethyl phenyl sulfide (8-12% yields), and SO₂ is liberated. The other reaction products are, respectively, the dibutyl and diphenyl disulfides (60-70% yields), HCl, and H₂O. 2. Apparently, the formation of β-chloroethyl butyl sulfide and β-chloroethyl phenyl sulfide is associated with the addition of the thiyl radical to the double bond of vinylsulfonyl chloride and subsequent rearrangement of the RSCH₂CHSO₂Cl radicals, with the migration of chlorine from sulfur to the adjacent carbon atom.