REACTIONS OF THIOL ESTERS WITH HALOGENS AND SOME N-HALO AND O-HALO COMPOUNDS

Abstract

S-Phenyl thioacetate (1) quantitatively reacted with 1/2 mole of bromine (or chlorine), yielding acetyl bromide (or chloride) and phenyl disulfide. With iodine, 1 formed a complex, which reacted with an alcohol (MeOH, Me₃CCH₂OH, PhCH₂OH), forming the corresponding ester; a catalytic amount of iodine was sufficient for this transesterification. 1 reacted quantitatively with 1-chlorobenzotriazole. The reaction of 1 with t-butyl hypochlorite yielded t-butyl acetate (70%) and acetyl chloride(30%).