Chlorotropic rearrangements of an α-sulfanyl-α-sulfonylalkanesulfenyl chloride to an α-chloroalkyl disulfide and an S-(α-chloroalkyl) thiosulfonate

Abstract

(1-Adamantylsulfonyl)(pentachlorophenylsulfanyl)chloromethanesulfenyl chloride, 3, can undergo two quantitative chlorotropic rearrangements, the more facile one leading to (1-adamantylsulfonyl)dichloromethyl pentachlorophenyl disulfide, 4, the less facile one forming S-[(pentachlorophenylsulfanyl)dichloromethyl] adamantane-1-thiosulfonate 5.