Thiosulfonate Explained

Thiosulfonates are organosulfur compounds with the formula RSO₂SR'. The parent member 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, 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.

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

1. Thiosulfonates: Synthesis, Reactions and Practical Applications. Nikolai S.. Zefirov. Nikolai V.. Zyk. Elena K.. Beloglazkina. Andrei G.. Kutateladze. Sulfur Reports. 1993. 14. 223–240. 10.1080/01961779308055018.
2. Preparation of S-Methyl Methanethiosulfonate from Dimethyl Sulfoxide Initiated by Oxalyl Chloride. Xixuan Zhao, Shuai Peng, Hao Wang, Shuai Huang, Baoguo Sun, Hongyu Tian and Sen Liang . Organic Syntheses. 2024. 101. 395. 10.15227/orgsyn.101.0395.
3. Trimethylene Dithiotosylate And Ethylene Dithiotosylate. R. B. Woodward . I. J. Pachter . Monte L. Scheinbaum . Org. Synth.. 1974. 54. 33. 10.15227/orgsyn.054.0033.