Mechanism of Interaction of γ-Halogenated Salts of Pyrylium and Benzopyrylium with Aromatic Amines |
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| Authors: | A O Manyashin A I Fomenko V N Storozhenko N T Berberova |
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| Institution: | (1) Astrakhan State Technical University, ul. Tatishcheva 16, Astrakhan, 414025, Russia |
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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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| Keywords: | nucleophilic substitution heteroaromatic compounds pyrylium flavylium single-electron process cyclic voltammetry charge-transfer complex |
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