Sulfinic acid chlorides mercaptans

Oxidations by chlorine are limited to only few types of compounds. In organic solvents and pyridine [681] or hexamethylphosphoramide (HMPA) [682] as cosolvents, primary alcohols are oxidized to aldehydes and secondary alcohols to ketones [681, 682]. Secondary alcohols are oxidized in preference to primary alcohols [681]. Many oxidations with chlorine are carried out in aqueous media and involve sulfur-containing compounds. Mercaptans [683], alkyl thiolcarboxylates [683], thiocyanates [684], isothioureas [684], disulfides [655], and sulfinic acids [656] are transformed into sulfonyl chlorides. The chlorination of dimethyl disulfide in acetic anhydride yields methanesulfinyl chloride [657]. 

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