Abstract
It is shown that in mixed reductive coupling of activated olefins A and B, in which A is reduced at the more anodic voltage, the ratio of cross‐coupled product HABH to self‐coupled product HAAH rises substantially as the controlled potential is made more negative. Diethyl maleate (DEM) was chosen as an example of A and ethyl acrylate (EA) and acrylonitrile (AN) as examples of B. Previously reported fluctuations of voltage along the cathode surface are confirmed and may lead to unexpected formation of HBBH. The results of cyclic voltammetry of DEM in the presence of EA or AN and of a kinetic study of the addition of a carbanion to these same acceptors in bulk are interpreted to indicate that the reductive coupling of DEM with the acceptors occurs largely but not exclusively at the electrode surface.
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