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. The simplest thiosulfonate, CH₃SO₂SCH₃ can however be prepared from dimethyl sulfoxide by treatment with oxalyl chloride.

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.

Oxidation with mCPBA gives disulfones.