The relative stabilities of σ- and π-complexes in aromatic benzofuran protonation have been studied by various methods. The results of CNDO/2 and INDO calculations on the one hand and STO-3G computations on the other support different explanations of the experimental facts. Our results give a theoretical foundation to Olah's suggestion with regard to a two-step mechanism for some electrophilic substitutions.
E. Silla, J. Bertrán, E. Canadell and J. I. Fernández-Alonso, J. Chem. Soc., Perkin Trans. 2, 1976, 1789 DOI: 10.1039/P29760001789
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