Abstract
Cyclic voltammograms for the reduction of cyclohexanecarbonyl chloride at a hanging mercury drop electrode in acetonitrile exhibit one wave when tetraethylammonium perchlorate is the supporting electrolyte and three waves when tetramethylammonium perchlorate is the supporting electrolyte; the single wave seen in the presence of tetraethylammonium perchlorate and the first wave observed in the presence of tetramethylammonium perchlorate are attributable to the one‐electron scission of the carbon‐chlorine bond. Controlled‐potential electrolyses of cyclohexanecarbonyl chloride at a potential causing cleavage of the carbon‐chlorine bond lead to production of cyclohexanecarboxaldehyde and 1,2‐dicyclohexylethene‐1,2‐diol dicyclohexanoate; cyclohexanecarboxylic acid, arising from hydrolysis of the starting material, reacts with unreduced acyl chloride to yield cyclohexanecarboxylic acid anhydride. Experiments involving the use of and deuterium oxide, as well as the appearance of small amounts of dicyclohexyl ketone and dicyclohexylethanedione, have confirmed that cyclohexanecarboxaldehyde is formed exclusively via an electrogenerated acyl radical intermediate.
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