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Vorobyev, Stepan V.; Primerova, Olga V.; Bylikin, Sergey Yu. and Koshelev, Vladimir N.
(2021).
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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About
- Item ORO ID
- 78992
- Item Type
- Journal Item
- ISSN
- 1878-5352
- Keywords
- Organic synthesis; Phenols; Lactams; Spectroscopic techniques; Quantum-chemical calculations; Mechanism study
- Academic Unit or School
-
Faculty of Science, Technology, Engineering and Mathematics (STEM) > Life, Health and Chemical Sciences
Faculty of Science, Technology, Engineering and Mathematics (STEM) - Copyright Holders
- © 2021 The Authors
- Depositing User
- ORO Import