Oxidation and Homolytic Coupling Regioselectivity of Carbazole in Acidie Media

Croatian Chemical Society 1997

Using voltammetric technique with a rotating disk electrode, the anodic oxidation of carbazole in aqueous H2S04 - ethanol mixtures was shown to proceed under diffusion and electron transfer control conditions. Electro-oxidation involves one electron transfer; electrode passivation occurs due to the formation of a poorly soluble product. By means of the SCF MO LCAO INDO, AMI-UHF and PM3-UHF methods, oxidative coupling regioselectivity for carbazole has been elucidated. Chemical oxidation of carbazole by ammonium vanadate in sulphuric acid medium features the stoichiometry 1:2, first order in substrate and first order in oxidant, and leads to the occurrenee of the diimine dication of carbazole.

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