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ELECTROCHEMICAL OXIDATIVE AROMATIZATION OF 9-SUBSTITUTED 9,10-DIHYDROACRIDINES: CLEAVAGE OF C–H vs C–X BOND

Oleg N. Chupakhin, Alexandr V. Shchepochkin, Valery N. Charushin, Anna V. Maiorova, Tatyana V. Kulikova, Konstantin Yu. Shunyaev, Andrey N. Enyashin, Pavel A. Slepukhin, Anna I. Suvorova
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Abstract


Reactivity of dihydroacridines bearing a С–X fragment at the geminal C-9 atom (where X = C, N, O, P, S) on anode has been investigated by means of electrochemical oxidation and thermodynamic and quantum-chemical calculations. The electrochemical oxidation results either in the formation of the 9-substituted acridines or in the cleavage of the C–X bond. This dual behavior of dihydroazines is analogous to processes reported in literature that take place upon treatment with chemical oxidants.

Keywords


acridines; dihydroacridines; bond dissociation energy; C–H functionalization; electrochemical oxidation; SNH reactions; thermodynamic studies

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