Trifluoroethyl benzyl sulfide was prepared (in 2-propanol) and subsequently chlorinated as a further test of substituent electronegativity based regiochemical predictions. The initial attempt to prepare that sulfide by reaction of 2, 2, 2-trifluoroethyl methanesulfonate and benzyl mercaptide anions (in methanol) furnished benzyl methyl sulfide. Mechanistic possibilities are discussed in detail and some synthetic consequences of this novel ...
