Thiosulfonate
Thiosulfonate esters are organosulfur compounds with the formula R−SO2−S−R'. The parent member S-methyl methanethiosulfonate CH3−SO2−S−CH3 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]
Thiosulfonate also refers to the thiosulfonate anion R−S2O−2 and its salts. Alkali metal organylthiosulfonates are the salts of organylthiosulfonic acids (e.g., sodium methanethiosulfonate CH3−S2O−2Na+). They are prepared by the reaction of organosulfonyl chlorides with sources of sulfide.[1][3]
Oxidation with mCPBA gives disulfones.[1]
See also
[edit]- Bunte salts are related organosulfur compounds containing the anion with the formula R−S−SO−3
- Thiosulfinate a structurally analogous compound containing functional group in a lower oxidation state, with the formula R−S(O)−S−R
- S-methyl methanethiosulfonate CH3−SO2−S−CH3
References
[edit]- ^ 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.
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