Lactamomethylation of alkylphenols: Synthesis and quantum-chemical study of the reaction pathway |
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Institution: | 1. Department of Organic Chemistry and Petroleum Chemistry, Faculty of Chemical and Environmental Engineering, Gubkin University, Moscow, Russia;2. The Open University, Walton Hall, Milton Keynes, MK7 6AA, UK |
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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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Keywords: | Organic synthesis Phenols Lactams Spectroscopic techniques Quantum-chemical calculations Mechanism study |
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