Electrohydrodimerization of 4,4-DIMETHYL-2-CYCLOHEXEN-1-ONE (cas 1073-13-8) in dimethylformamide on a mercury electrode

Add time:07/25/2019    Source:sciencedirect.com

Electrohydrodimerization of 4,4-DIMETHYL-2-CYCLOHEXEN-1-ONE (cas 1073-13-8) in dimethylformamide with 0.1 M tetrabutylammonium perchlorate as supporting electrolyte has been studied by polarography, cyclic voltammetry and controlled-potential electrolysis. A one-electron reduction process is found, which leads to the formation of the pinacol 4,4,4′,4′-tetramethyl-(bi-2-cyclohexen-1-yl)-1,1′-diol. Voltammetric data show that the process occurs through a radical-radical coupling pathway in which the dimerization reaction follows the initial one-electron charge transfer and takes place in a reaction layer much thinner than the diffusion layer. Then, the final pinacol is formed via dimerization of the initially electrogenerated radical anion and further protonation of the resulting dimer dianion. The standard rate constant of the initial one-electron charge transfer, determined by cyclic voltammetry at scan rates higher than 1 V s−1, is found to be 1.51×10−2 cm s−1. Under polarographic conditions and when the reduction process is irreversible in cyclic voltammetry (at scan rates lower than 1 V s−1), the dimerization reaction is the rate-determining step of the pathway.

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