Journal of the Brazilian Chemical Society
versão impressa ISSN 0103-5053
CURI, Denise; PARDINI, Vera L. e VIERTLER, Hans. Electrochemical Oxidation of Ketenedithioacetals. J. Braz. Chem. Soc. [online]. 1998, vol.9, n.1, pp. 69-77. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50531998000100013.
Anodic oxidation of ketenedithioacetals 1, R1R2C=C(SMe)2, is reported in this work. Cyclic voltammetry performed in dry MeCN 0.1 M NaClO4 using Pt bead as anode and Ag/AgI as reference electrode showed an irreversible oxidation step. The corresponding oxidation peak potentials were slightly dependent on the carbon-carbon double bond substitution pattern (tri- vs. tetrasubstitution) but showed a strong dependence upon the nature of the R groups. The main products of the controlled potential preparative electrolyses in 0.2 M NaClO4 aqueous acetonitrile were dimers for R1 = n-Pr or C6H5C(O) and R2 = H, and a-hydroxy-thioesters and monosulfoxides for the substrates with tetrasubstituted carbon-carbon double bonds.
Palavras-chave : ketenedithioacetals; electrochemical oxidation.