Chlorinolyses of Alkyl (or Aryl) Phthalimidomethyl Sulfides with Sulfuryl Chloride or Chlorine in the Presence and the Absence of Acetic Anhydride

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Alkyl and aryl phthalimidomethyl sulfides give alkane- and arenesulfenyl chlorides on reaction with equimolar sulfuryl chloride or molecular chlorine in an aprotic solvent at room temperature, but give alkane- and arenesulfinyl chlorides on reaction with two molar equivalents of the same reagent in the presence of acetic anhydride under the same conditions. The utility of these reactions for the synthesis of organo sulfenyl chlorides and sulfinyl chlorides was confirmed.