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Influence of polar substituent effects in the acylation of phenols

Conclusions

  1. 1.

    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.

  2. 2.

    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.

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Literature cited

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    S. V. Vinogradova, V. A. Vasnev, V. V. Korshak, T. I. Mitaishvili, and A. V. Vasil'ev, Dokl. Akad. Nauk SSSR,187, 1297 (1969).

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    V. N. Bazhulina, S. V. Bogatkov, E. Ya. Borisova, and E. M. Cherkasova, Zh. Organ. Khim.,5, 1421 (1961).

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    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).

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    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).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2138–2140, September, 1970.

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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

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Keywords

  • Chloride
  • Phenol
  • Catalysis
  • Reaction Mechanism
  • Acidic Phenol