Electrochemical Oxidation of Ketenedithioacetals

• Autor(a) principal: Curi,Denise
• Data de Publicação: 1998
• Outros Autores: Pardini,Vera L., Viertler,Hans
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000100013
• topic: ketenedithioacetals; electrochemical oxidation

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 alpha-hydroxy-thioesters and monosulfoxides for the substrates with tetrasubstituted carbon-carbon double bonds.