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Issue 12, 1972
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Anodic oxidation of Schiff bases. Part I. Oxidation of N-benzylidene-p-anisidines in acetonitrile

Abstract

The anodic oxidations of several N-benzylidene-p-anisidines have been investigated by cyclic voltammetry and controlled potential electrolysis at a glassy-carbon electrode in acetonitrile. All the compounds tested were oxidized irreversibly. N-Benzylidene-p-anisidines showed two anodic waves. The relationship between the peak potentials of their first wave and the σ+ values of the substituents on the benzylidene group was linear, whereas that for the second wave was not. On controlled potential electrolysis at the first wave, protonated benzylidene-p-anisidines were identified, and on electrolysis at the potential of the second wave, p-benzoquinone imine and the corresponding benzaldehyde were identified as the main products. When water was added to the solution, the second wave shifted to a lower potential, whereas the potential of the first wave remained unchanged. Hence a combined wave was observed in the presence of sufficient water. On controlled potential electrolysis in the presence of 5% water, p-benzoquinone and the corresponding benzaldehyde were formed as the main products. Analysis of the minor product suggested that the p-anisidine radical cation was formed as an intermediate. A possible reaction mechanism is suggested.

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Article type: Paper
DOI: 10.1039/P29720001882
J. Chem. Soc., Perkin Trans. 2, 1972, 1882-1887

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    Anodic oxidation of Schiff bases. Part I. Oxidation of N-benzylidene-p-anisidines in acetonitrile

    M. Masui and H. Ohmori, J. Chem. Soc., Perkin Trans. 2, 1972, 1882
    DOI: 10.1039/P29720001882

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