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Abstract
The electrohydrodimerization reaction of dimethyl fumarate in the presence of cinnamonitrile and acrylonitrile was studied in dimethylformamid e solution by rotating ring-disk emctrode, voltammetric and coulometric techniques. At potentials where only dimethyl fumarate is electroactive, the rate and mechanism of decay of the dimethyl fumarate anion radical are only slightly perturbed from the results obtained in the absence of cinnamonitrile and acrylonitrile. This is an indication that little or no cross-coupling was occurring. At potentials where both dimethyl fumarate and cinnamonitrile are electroactive evidence for the occurrence of a solution oxidation-reduct ion reaction consuming cinnamonitrile anion radical and dimethyl fumarate parent was obtained. In addition, the role of cis-trans isomerization of radical anions in electrohydrodimerization reactions is discussed. Differences in the cyclic voltammograms of diethyl maleate in the presence of acrylonitrile when compared with those obtained in the absence of acrylonitrile and for dimethyl fumarate in the presence of acrylonitrile are observed. We have previously reported (1) the use of rotating ring-disk electrode (RRDE) voltammetry, cyclic voltammetry, and coulometry in the elucidation of the mechanism of the electrohydrodimerization (electrolytic reductive coupling) of the three di-substituted olefins dimethyl fumarate (DF), cinnamonitrile (CN), and fumaronitrile (FN) in anhydrous dimethylformamide (DMF) solution. Potential-step chronoamperometry has also been employed to determine the electrohydrodimerization mechanism of diethyl fumarate (2). These studies showed that these hydrodimerizations proceed predominantly via a one-electron reduction
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