Chlorocarbonylsulfenyl chloride

Chlorocarbonylsulfenyl chloride is the chemical compound with the formula. It is a colorless, distillable liquid that is related to phosgene. It features two reactive functional groups, an acyl chloride and a sulfenyl chloride. According to X-ray crystallography, the molecule is planar.

Preparation and reactions

Chlorocarbonylsulfenyl chloride is prepared by hydrolysis of trichloromethane sulfenyl chloride in sulfuric acid as solvent:
The compound, being bifunctional, has been used for the preparation of several heterocycles including oxathiazol-2-ones, oxathialones, and oxathiazoles.
Treatment with formamides gives dithiazolidinediones.
Relevant to amino acid chemistry, ethoxythiocarbonyl amides react with chlorocarbonylsulfenyl chloride to give DTS derivatives: