Thiosulfonate
Thiosulfonates are organosulfur compounds with the formula RSO2SR'. The parent member CH3SO2SCH3 is a colorless liquid.
Thiosulfonate esters are usually produced by oxidation of disulfides or the nucleophilic attack of thiolates on organosulfonyl halides.[1] The simplest thiosulfonate, CH3SO2SCH3 can however be prepared from dimethyl sulfoxide by treatment with oxalyl chloride.[2]
Alkali metal thiosulfonates are the conjugate base of thiosulfuric acid. They are prepared by the reaction of organosulfonyl chlorides with sources of sulfide.[1][3]
Oxidation with mCPBA gives disulfones.[1]
See also
- Bunte salts are related organosulfur compounds with the formula RSSO3−
- Thiosulfinate a structurally analogous functional group in a lower oxidation state, with the formula RSS(O)R
References
- ^ a b c Zefirov, Nikolai S.; Zyk, Nikolai V.; Beloglazkina, Elena K.; Kutateladze, Andrei G. (1993). "Thiosulfonates: Synthesis, Reactions and Practical Applications". Sulfur Reports. 14: 223–240. doi:10.1080/01961779308055018.
- ^ Xixuan Zhao, Shuai Peng, Hao Wang, Shuai Huang, Baoguo Sun, Hongyu Tian and Sen Liang (2024). "Preparation of S-Methyl Methanethiosulfonate from Dimethyl Sulfoxide Initiated by Oxalyl Chloride". Organic Syntheses. 101: 395. doi:10.15227/orgsyn.101.0395.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ R. B. Woodward; I. J. Pachter; Monte L. Scheinbaum (1974). "Trimethylene Dithiotosylate And Ethylene Dithiotosylate". Org. Synth. 54: 33. doi:10.15227/orgsyn.054.0033.