thiosulfonate

{{Short description|Class of chemical compounds}}

{{confuse|Sulfonyl group}}

File:RSO2SR'.png

Thiosulfonate esters are organosulfur compounds with the formula {{chem2|R\sSO2\sS\sR'}}. The parent member S-methyl methanethiosulfonate {{chem2|CH3\sSO2\sS\sCH3}} is a colorless liquid.

Thiosulfonate esters are usually produced by oxidation of disulfides or the nucleophilic attack of thiolates on organosulfonyl halides.{{cite journal|title=Thiosulfonates: Synthesis, Reactions and Practical Applications|first1=Nikolai S.|last1=Zefirov|first2=Nikolai V.|last2=Zyk|first3=Elena K.|last3=Beloglazkina|first4=Andrei G.|last4=Kutateladze|journal=Sulfur Reports|year=1993|volume=14|pages=223–240|doi=10.1080/01961779308055018}} The simplest thiosulfonate, {{chem2|CH3SO2SCH3}} can however be prepared from dimethyl sulfoxide by treatment with oxalyl chloride.{{cite journal|title=

Preparation of S-Methyl Methanethiosulfonate from Dimethyl Sulfoxide Initiated by Oxalyl Chloride|author=

Xixuan Zhao, Shuai Peng, Hao Wang, Shuai Huang, Baoguo Sun, Hongyu Tian and Sen Liang |journal= Organic Syntheses|year=2024|volume=101|page=395|doi=10.15227/orgsyn.101.0395}}

Thiosulfonate also refers to the thiosulfonate anion {{chem2|R\sS2O2-}} and its salts. Alkali metal organylthiosulfonates are the salts of organylthiosulfonic acids (e.g., sodium methanethiosulfonate {{chem2|CH3\sS2O2-Na+}}). They are prepared by the reaction of organosulfonyl chlorides with sources of sulfide.{{cite journal|title=Trimethylene Dithiotosylate And Ethylene Dithiotosylate|author=R. B. Woodward |author2=I. J. Pachter |author3=Monte L. Scheinbaum |journal=Org. Synth.|year=1974|volume=54|page=33|doi=10.15227/orgsyn.054.0033}}

Oxidation with mCPBA gives disulfones.