Abstract
The reaction of sodium phenacylthiosulfate with amine was found to form acetophenone as by-product and elucidated to proceed through the intermediate formation of diphenacyl disulfide. The reaction between sodium ethoxycarbonylmethylthiosulfate with cyclohexylamine was also confirmed to proceed analogously through the formation of diethoxycarbonylmethyl disulfide, but not sodium cyclohexylcarbamoylmethylthiosulfate and dicyclohexylcarbamoylmethyl disulfide, to give N, N'-dicyclohexylthiooxamide and cyclohexylammonium cyclohexylaminothiocarbonylcarboxylate. Furthermore, the salt was proved to be formed via the intermediate ethoxycarbonyl-N-cyclohexylthiocarboxamide, but not by hydrolysis of N, N'-dicyclohexylthiooxamide.
