Oxidation of γ-stannyl sulfides by monochloramine CB and hydrogen peroxide

The first γ-trimethylstannyl sulfimide, Me³Sn(CH₂)₃S(=NSO₂Ar)C₅H₁₁-n, was synthesized by oxidative imination of Me₃Sn(CH₂)₃SC₅H₁₁-n with ArSO₂(Na)Cl (Ar=C₆H₄Cl-4). Oxidation of γ-trimethylstannyl sulfimide by an alkaline solution of H₂O₂ gave γ-trimethylstannyl sulfoximide, Me₃Sn(CH₂)₃S(O)(=NSO₂Ar)C₅H₁₁-n, and γ-trimethylstannyl sulfone, Me₃Sn(CH₂)₃SO₂C₅H₁₁-n, the latter compound resulting from hydrolysis of the arylsulfimide group. Oxidation of stannyl sulfide by hydrogen peroxide yielded γ-trimethylstannyl sulfoxide, Me₃Sn(CH₂)₃S(O)C₅H₁₁-n (under mild conditions) or γ-trimethylstannyl sulfone (under more severe conditions). Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 371–374, February, 1997.