A. Esteves, D. M. Goken, L. Klein
Dec 15, 2003
Citations
0
Influential Citations
13
Citations
Journal
Journal of Electroanalytical Chemistry
Abstract
Abstract Cyclic voltammograms for the reduction of ethyl 2-bromo-3-(3 ′ ,4 ′ -dimethoxyphenyl)-3-(propargyloxy)propanoate ( 1 ) at glassy carbon electrodes in dimethylformamide containing tetraalkylammonium salts exhibit three prominent waves corresponding to cleavage of the carbon–bromine bond and to subsequent reduction of ethyl trans -3-(3 ′ ,4 ′ -dimethoxyphenyl)-prop-2-enoate ( 4 ). Controlled-potential electrolyses of 1 at potentials corresponding to reduction of the carbon–bromine bond afford 4 as the major product with an average yield of 56%. In the presence of a proton donor (1,1,1,3,3,3-hexafluoro-2-propanol), the quantity of 4 decreases slightly, and 2-(3 ′ ,4 ′ -dimethoxyphenyl)-3-(ethoxycarbonyl)-4-methyl-2,5-dihydrofuran ( 3 ) is obtained in moderate amount (∼26%). We propose a mechanistic scheme whereby the major products are formed via a combination of one- and two-electron processes.