Analogous mechanism intermediacy of chlorosulfonium salt of type 6 has been suggested for chlorinolysis of alkyl arylsylfenates in AcOH (Ref 7b). We have shown that this reaction in the presence of lithium perchlorate gives covalent perchlorates. For instance, -2-chlorocyclohexyl 2,4-dinitrophenylsulfenate reacts with chlorine in AcOEt in the presence of 5 mol-eqv of lithium perchlorate to give 2-chlorocyclohexyl perchlorates 2 (40% yield) and 3 (27% yield).
