Interaction of 2-unsubstituted imidazole N-oxides with electron-deficient olefins: a quantum chemical analysis.

Autor:	Selivantev, Yu. M., Mityanov, V. S., Uvarova, E. S., Kolokolov, F. A., Morozov, A. N., Raitman, O. A.
Předmět:	POTENTIAL energy surfaces DENSITY functional theory ANALYTICAL chemistry ELECTRON-deficient compounds ACRYLONITRILE
Zdroj:	Russian Chemical Bulletin; Sep2024, Vol. 73 Issue 9, p2593-2605, 13p
Abstrakt:	Reactions between the model compound N-1,4,5-trimethyl-1H-imidazole-3-oxide and electron-deficient olefins including 2-(4-methoxybenzylidene)malononitrile, (E)-ethyl-2-cyano-3-(4-methoxyphenyl)acrylate, 2-benzoyl-3-(4-methoxyphenyl)acrylonitrile, and 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione were theoretically studied in terms of the density functional theory. It was demonstrated that the reactions can proceed either by the 1,3-dipolar cycloaddition mechanism or by the Michael addition mechanism depending on the type of electron-withdrawing substituents in the olefin molecule. The reaction pathways were calculated and the intermediate structures were determined. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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