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

Arabian Journal of Chemistry

Olga V. Primerova¹  Stepan V. Vorobyev²  Sergey Yu. Bylikin²  Vladimir N. Koshelev³ 

[1] Corresponding author.;Department of Organic Chemistry and Petroleum Chemistry, Faculty of Chemical and Environmental Engineering, Gubkin University, Moscow, Russia;The Open University, Walton Hall, Milton Keynes, MK7 6AA, UK;

关键词: Organic synthesis;    Phenols;    Lactams;    Spectroscopic techniques;    Quantum-chemical calculations;    Mechanism study;   

DOI  :  

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown