Thiosulfonate

Not to be confused with Sulfonyl group.

Structure of thiosulfonate ester.

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

• 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

1. 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.
2. 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.
3. 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.