Abstract
The kinetics of benzoylation of substituted phenols with benzoyl chloride in the presence of pyridine N-oxide-triethylamine was analyzed with regard to previously reported data on benzoylation, phosphorylation, and sulfonylation of phenols and carboxylic acids. A common mechanism of the synergistic effect was established. The synergistic effect decreases in the series PhCOCl >> (EtO)2POCl > TsCl.
Similar content being viewed by others
REFERENCES
Savelova, V.A., Belousova, I.A., Simanenko, Yu.S., and Titskii, G.D., Zh. Org. Khim. 1987, vol. 23, no. 7, pp. 1571-1572.
Savelova, V.A., Belousova, I.A., Simanenko, Yu.S., and Prokop'eva, T.M., Zh. Org. Khim. 1989, vol. 25, no. 4, pp. 677-684.
Savelova, V.A., Belousova, I.A., and Simanenko, Yu.S., Zh. Org. Khim. 1991, vol. 27, no. 12, pp. 2592-2604.
Savelova, V.A., Belousova, I.A., and Simanenko, Yu.S., Zh. Org. Khim. 1994, vol. 30, no. 2, pp. 236-242.
Simanenko, Yu.S., Belousova, I.A., and Savelova, V.A., Russ. J. Org. Chem. 1996, vol. 32, no. 4, pp. 591-602.
Belousova, I.A., Simanenko, Yu.S., Savelova, V.A., and Suprun, I.P., Russ. J. Org. Chem. 2001, vol. 37, no. 7, pp. 969-974.
Belousova, I.A., Simanenko, Yu.S., Savelova, V.A., and Suprun, I.P., Russ. J. Org. Chem. 2000, vol. 36, no. 11, pp. 1656-1664.
Belousova, I.A., Simanenko, Yu.S., Savelova, V.A., Mitchenko, R.S., and Suprun, I.P., Ukr. Khim. Zh. 2001, no. 4, pp. 94-98.
Savelova, V.A., Belousova, I.A., Litvinenko, L.M., and Yakovets, A.A., Dokl. Akad. Nauk SSSR 1984, vol. 274, no. 6, pp. 139-31398.
Chotii, K.Yu. Rybachenko, V.I., and Titov, E.V., Zh. Obshch. Khim. 1987, vol. 57, no. 7, pp. 1612-1616.
Emanuel', N.M. and Knorre, D.G., Kurs khimicheskoi kinetiki (Lectures on Chemical Kinetics), Moscow: Vysshaya Shkola, 1974, p. 136.
Gordon, A.J. and Ford, R.A., The Chemist's Companion New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 440.
Litvinenko, L.M., Titskii, G.D., and Shpan'ko, I.V., Zh. Org. Khim. 1971, vol. 7, no. 1, pp. 107-113.
Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Jr., Organic Solvents: Physical Properties and Methods of Purification New York: Intersci., 1955, 2nd ed. Translated under the title Organicheskie rastvoriteli, Moscow: Inostrannaya Literatura, 1958, p. 431.
Dictionary of Organic Compounds Heilbron, J. and Bunbury, H. M., Eds., London: Eyre and Spottswoode, 1953, vols. 1-3.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Belousova, I.A., Savelova, V.A., Simanenko, Y.S. et al. Synergistic Effect in the Catalysis by Pyridine N-Oxide-Triethylamine Mixture of Acyl Transfer Processes with Participation of Benzoyl, Diethoxyphosphinoyl, and p-Toluenesulfonyl Chlorides. Russian Journal of Organic Chemistry 38, 111–114 (2002). https://doi.org/10.1023/A:1015319228542
Issue Date:
DOI: https://doi.org/10.1023/A:1015319228542