Abstract:
Global and local reactivity indexes indicate a polar character of the [2 + 3] cycloaddition of nitroethene to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone. The regioselectivity of the reactions is determined by the attack of an oxygen-centred nucleophilic site of the nitrone on the b-carbon atom in nitroethene, which is confirmed by B3LYP/6-31G(d) simulations of the reaction pathways. Although the transition complexes are considerably asymmetric and polar, the reactions proceed via a concerted mechanism.
Document Type:
Article
Language: English
Citation:
R. Jasiński, O. I. Koifman, A. Barański, “A DFT study on the regioselectivity and molecular mechanism of nitroethene [2 + 3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone”, Mendeleev Commun., 21:5 (2011), 262–263
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https://www.mathnet.ru/eng/mendc2937
https://www.mathnet.ru/eng/mendc/v21/i5/p262
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