New Dithio-bis-(diaroylmethanes) and Acetyl Diaroylchloromethyl Bisulfides: Attractive Synthons and Precursors for the Liberation of Highly Reactive Dithiiranes or Thiosulfines

Article abstract of DOI:10.1007/BF00807029

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), α-chlorosulfenic acid chlorides, and acetyl diaroylchloromethyl disulfides. The latter compounds are of interest for the liberation of highly reactive dithiirane/thiosulfine species. With thiomorpholine, α-chlorosulfenic acid chlorides give α-chlorosulfenic acid amides.