New dithio-bis-(diaroylmethanes) and acetyl diaroylchloromethyl disulfides: Attractive synthons and precursors for the liberation of highly reactive dithiiranes or thiosulfines

In a new, feasible procedure five symmetrical para-substituted diaroylmethanes ((4-X-C6H4-CO)(2)-CH2; X = F, Cl, Br, CH3, and CH3O) are prepared, in most cases in very good yields. For purification and activation, they are converted into the copper(II) complexes of their enolates. Subsequently, three reaction steps with disulfur dichloride (S2Cl2), chlorine, and ethanethioic acid yield new CH-acidic dithio-bis-(diaroylmethanes), alpha-chlorosulfenic acid chlorides, and acetyl diaroylchloromethyl disulfides. The latter compounds are of interest for the liberation of highly reactive dithiirane/thiosulfine species. With thiomorpholine, alpha-chlorosulfenic acid chlorides give alpha-chlorosulfenic acid amides.