Tetrahedron p. 249 - 254 (1987)
Update date:2022-08-11
Topics:
Miklos, Peter
Senning, Alexander
Oxidation of the Knoevenagel condensation products 2 of 3-oxo-tetrahydrothiophene (1) and active methylene compounds of the type Z-CH2-COOH with an H2O2/V2O5/t-BuOH reagent furnishes the corresponding sulfoxides 3 in excellent yields.The isomer distributions of the sulfides 2 and the sulfoxides 3 reflect peculiarities of hydrothiophenes as compared to similar open-chain systems and establish that the stabilizing effect of the sulfoxide group on β,γ-double bonds is greater than the corresponding effect of so strongly stabilizing groups as CN and COOR.
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