A DFT study on the regioselectivity and molecular mechanism of nitroethene [2+3] cycloaddition to (Z)-C,N-diphenylnitrone and C,C,N-triphenylnitrone

作者：Jasinski Radomir; Koifman Oskar I; Baranski Andrzej^*

来源：Mendeleev Communications, 2011, 21(5): 262-263.

DOI：10.1016/j.mencom.2011.09.010

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 beta-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.

• 出版日期2011-10