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Mechanism of Interaction of γ-Halogenated Salts of Pyrylium and Benzopyrylium with Aromatic Amines

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Abstract

Stoichiometry and kinetics of reactions of 2,6-diphenyl-4-chloropyrylium, 4-chloroflavylium, 4-bromoflavylium, and 4-iodoflavylium perchlorates with nucleophiles N,N-dimethylaniline and n-phenylenediamine are studied using cyclic voltammetry and spectroscopy. Nucleophilic substitution in these compounds proceeds via the formation of a charge-transfer complex, which converts into a radical ion pair as a result of the electron transfer. Heterolytic clevage of the C–Hal bond occurs at the stage of pyranyl (flavanyl) radical.

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Authors and Affiliations

  1. Astrakhan State Technical University, ul. Tatishcheva 16, Astrakhan, 414025, Russia

    A. O. Manyashin, A. I. Fomenko, V. N. Storozhenko & N. T. Berberova

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  1. A. O. Manyashin
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  2. A. I. Fomenko
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  3. V. N. Storozhenko
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  4. N. T. Berberova
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Correspondence to N. T. Berberova.

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Manyashin, A.O., Fomenko, A.I., Storozhenko, V.N. et al. Mechanism of Interaction of γ-Halogenated Salts of Pyrylium and Benzopyrylium with Aromatic Amines. Russian Journal of Electrochemistry 39, 1240–1244 (2003). https://doi.org/10.1023/B:RUEL.0000003453.71265.a2

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  • DOI: https://doi.org/10.1023/B:RUEL.0000003453.71265.a2

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