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

Klys, Arkadiusz; Czardybon, Wojciech; Warkentin, John; Werstiuk, Nick Henry
September 2005
Canadian Journal of Chemistry;Sep2005, Vol. 83 Issue 9, p1360
Academic Journal
Thermolysis of 2-acetoxy-5,5-dimethyl-2-methylthio-Δ3-1,3,4-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.


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