The polar effect of substituents during the acylation of phenols with benzoyl chloride in the presence of a strong tertiary amine corresponds to a scheme involving general base catalysis.
In the case of the relatively weak tertiary amine a shift in the reaction mechanism probably occurs on passing from the more acidic to the less acidic phenols: general base catalysis gives way to nucleophilic catalysis.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
S. V. Vinogradova, V. A. Vasnev, V. V. Korshak, T. I. Mitaishvili, and A. V. Vasil'ev, Dokl. Akad. Nauk SSSR,187, 1297 (1969).
V. N. Bazhulina, S. V. Bogatkov, E. Ya. Borisova, and E. M. Cherkasova, Zh. Organ. Khim.,5, 1421 (1961).
A. Albert and E. Sergeant, Ionization Constants of Acids and Bases [Russian translation], Nauka (1964), p. 126; C. H. Rochester, J. Chem. Soc., 4603 (1965); Z. M. Magnusson, C. Postmus, and C. A. Craig, J. Am. Chem. Soc.,85, 1711 (1963); B. S. Smolyakov andM. P. Primanchuk, Zh. Fiz. Khim.,40, 1842 (1966).
Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostovsk. Gos. Univ. (1966); pp. 85, 109, 349; M. T. Tribble and J. G. Traynham, J. Am. Chem. Soc.,91, 379 (1969).
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2138–2140, September, 1970.
About this article
Cite this article
Vinogradova, S.V., Vasnev, V.A., Korshak, V.V. et al. Influence of polar substituent effects in the acylation of phenols. Russ Chem Bull 19, 2018–2020 (1970). https://doi.org/10.1007/BF00849799
- Reaction Mechanism
- Acidic Phenol