Photocatalytic oxidation of several primary aliphatic amines on irradiated TiO2powders suspended in anhydrous acetonitrile led to good yields of the corresponding symmetrical N-alkylidene amines. Mechanistic electrochemical investigation of the reaction revealed intermediate formation of an immonium cation in an ECE route. This species is generated via electrooxidation of an α-amino radical formed by deprotonation of the primary oxidation product, an aminium cation radical. The influence of the metal oxide surface on radical cation reactivity is discussed. © 1986.
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