Thiosulfonate

Not to be confused with Sulfonyl group.

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.

Structure of thiosulfonate ester.

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