Lactamomethylation of alkylphenols: synthesis and quantum-chemical study of the reaction pathway

Vorobyev, Stepan V.; Primerova, Olga V.; Bylikin, Sergey Yu. and Koshelev, Vladimir N. (2021). Lactamomethylation of alkylphenols: synthesis and quantum-chemical study of the reaction pathway. Arabian Journal of Chemistry, 14(11), article no. 103424.

DOI: https://doi.org/10.1016/j.arabjc.2021.103424

Abstract

Six novel lactamomethyl derivatives of 2,5-dimethylphenol and 2,3,5-trimethylphenol were prepared with moderate yields by the reaction of corresponding phenols with 1-(hydroxymethyl)lactams in the presence of an acid catalyst. In all cases, the substitution occurred at position 4 to the phenolic hydroxyl group. The structures of all synthesized compounds were confirmed by FT-IR, 1H and 13C NMR, 2D NMR and elemental analysis. The selectivity and possible pathways of the lactamomethylation reaction were studied by quantum-chemical methods. In silico calculations showed that the substitution at para-position to the hydroxyl group of the corresponding phenols was more preferable due to the higher stability of forming intermediates.

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