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

Autor: A. O. Manyashin, A. I. Fomenko, V. N. Storozhenko, N. T. Berberova
Předmět:
Zdroj: Russian Journal of Electrochemistry; Nov2003, Vol. 39 Issue 11, p1240-1244, 5p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
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