dithiocarbonate

Dithiocarbonates are a class of organosulfur compounds with the general formula ROC(=S)SR'. They contain a dithiocarbonate functional group, which is characterized by a carbonyl group bonded to two sulfur atoms, with one sulfur atom also bonded to an alkyl or aryl group and the other sulfur atom bonded to a different alkyl or aryl group. Dithiocarbonates can be viewed as derivatives of carbonic acid where both oxygen atoms have been replaced by sulfur atoms. They are structurally related to xanthates, which have the formula ROC(=S)SR'.

These compounds are typically synthesized through reactions involving carbon disulfide. For example, they can be formed by the reaction of alkoxides with carbon disulfide in the presence of an alkyl halide, or by the reaction of thiols with dialkyl dithiocarbonates. Dithiocarbonates are often employed as intermediates in organic synthesis. Their reactivity stems from the presence of the thionoester group and the sulfur atoms, which can participate in various nucleophilic and electrophilic reactions. They have found applications in areas such as the synthesis of heterocycles, as ligands in coordination chemistry, and in certain polymerization processes. The specific properties and reactivity of dithiocarbonates depend on the nature of the R and R' substituents.