Reactions of acetoxy(methylthio)carbene and S-methyl thiopyruvate

Thermolysis of 2-acetoxy-5,5-dimethyl-2-methylthio-Δ 3 -1,3,4-oxadiazoline in benzene at 110 °C afforded S-methyl 2-oxopropanethioate (S-methyl thiopyruvate) from 1,2-acyl migration in acetoxy(methylthio)carbene, as well as S,S-dimethyl 2-acetoxy-2-methylpropanebis(thioate) and S-methyl 2-acetoxy-2-(methylthio)butanethioate. The latter two, both composed of two carbene units, are derived from reaction of the first product with the carbene.Key …