Synthesis of unsymmetrical thiosulfonate derivatives

Thiosulfonates (R1SO2SR2) are organosulfur compounds also known as the S-esters of thiosulfonic acid. They are produced by the oxidation of disulfides or by the reaction of organosulfonyl halides with thiolates. Thiosulfonates contain a disulfide bond where one of the sulfur atoms bears two oxygen atoms. These interesting compounds are more reactive than disulfides and are able to react with both nucleophiles and electrophiles since the oxidation states of the two sulfur atoms are different, oxidation state II for the -SR2 and oxidation state VI for the R1SO2-. Moreover, they can react as sulfenylating or as sulfonylating reactants depending on the reaction conditions. Organosulfur compounds, including thiosulfonates, are present in many natural products and are used as building blocks in organic synthesis. Furthermore, thiosulfonates are used in pharmaceuticals, they have demonstrated a wide range of biological activities including anti-microbial, anti-obesity, anti-fungal, and anti-cancer activities. In this study, a range of thiosulfonate derivatives were obtained by the reaction of potassium p-toluenthiosulfonate with various p-substituted benzyl halogens in the presence of DMF at room temperature. The compounds were characterized by H-NMR, C-NMR, IR and their melting points determined.