Abstract
Abstract Cathodic behavior of N-cyclohexylidenepyrrolidinium salt (1) and N-cyclohexylideneaniline (2) in acetonitrile has been studied by means of dc polarography, cyclic voltammetry and preparative electrolysis under controlled potential conditions. The compound 1 exhibits a reduction wave at about −1.8 V, which is accompanied by formation of a surface compound. The products obtained from the preparative electrolysis were neither saturated amines nor dimeric compounds but were mostly polymeric materials. However, when electrophilic olefins, such as acrylonitrile or methyl acrylate, were present in the solution, coupling products were produced. The compound 2, which cannot be reduced by itself below −2.7 V, is reduced at about −1.8 V when benzoic acid is in the solution. The reduction product in this case was N-cyclohexylaniline, which was replaced by a coupling product when acrylonitrile was present in the reaction system. The formation of the coupling products is considered to occur by a radical mechanism in both cases.
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