Abstract
The rate of formation of N- and O-acetyl and benzoyl salts of pyridines and pyridine N-oxides in acetonitrile and methylene chloride and equilibria therein were studied. The process occurs in one step following the SN2 mechanism with a small degree of bond rupture in the transition state.
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REFERENCES
Jencks, W.P., Catalysis in Chemistry and Enzymology, New York: Dower, 1987.
Litvinenko, L.M. and Oleinik, N.M., Mekhanizmy deistviya organicheskikh katalizatorov: Osnovnyi i nukleofil'nyi kataliz (Mechanisms of Action of Organic Catalysts: Base and Nucleophilic Catalysis), Kiev: Naukova Dumka, 1984, p. 263.
Fersht, A.R. and Jencks, W.P., J. Am. Chem. Soc., 1969, vol. 91, p. 2125.
Titov, E.V., Chotii, K.Yu., and Rybachenko, V.I., Zh. Obshch. Khim., 1981, vol. 51, p. 682.
Savelova, V.A., Belousova, I.A., Litvinenko, L.M., and Yakovets, A.A., Dokl. Akad. Nauk SSSR, 1984, vol. 274, p. 1393.
Savelova, V.A. and Oleinik, N.M., Mekhanizmy deistviya organicheskikh katalizatorov (Mechanisms of Action of Organic Catalysts), Kiev: Naukova Dumka, 1990, p. 296.
Savelova, V.A., Popov, A.F., Solomoichenko, T.N., Sadovskii, Yu.S., Piskunova, Zh.P., and Lobanova, O.V., Russ. J. Org. Chem., 2000, vol. 36, p. 1465.
Titskii, G.D. and Turovskaya, M.K., Ukr. Khim. Zh., 1993, vol. 59, p. 423.
Titskii, G.D., Turovskaya, M.K., and Yakovets, A.A., Mendeleev Commun., 1995, no. 4, p. 161.
Titskii, G.D., Turovskaya, M.K., and Korzhenevskaya, N.G., Ukr. Khim. Zh., 1996, vol. 62, p. 58.
Rybachenko, V.I., Chotii, K.Yu., Kozhevina, L.I., and Titov, E.V., Zh. Fiz. Khim., 1984, vol. 58, p. 1341.
Chotii, K.Yu., Rybachenko, V.I., and Titov, E.V., Zh. Obshch. Khim., 1987, vol. 57, p. 1612.
Semenova, R.G., Gol'dshtein, I.P., Grebenyuk, L.V., Makarova, R.A., and Rybachenko, V.I., Zh. Fiz. Khim., 1997, vol. 71, p. 235.
Reimers, J.R. and Hall, L.E., J. Am. Chem. Soc., 1999, vol. 121, p. 3730.
Schroeder, G., Leska, B., Gierczyk, B., and Rybachenko, V.I., Pol. J. Chem., 2001, vol. 75, p. 1947.
Linert, W. and Jameson, R.F., Chem. Soc. Rev., 1989, vol. 18, p. 477.
Titov, E.V., Makarova, R.A., Rybachenko, V.I., Chotii, K.Yu., and Goncharova, L.D., Teor. Eksp Khim., 1988, vol. 24, p. 227.
Titov, E.V., Rybachenko, V.I., Goncharova, L.D., and Semenova, R.G., Zh. Fiz. Khim., 1980, vol. 54, p. 3099.
Shmid, R. and Sapunov, V.N., Neformal'naya kinetika (Informal Kinetics), Moscow: Mir, 1985, p. 263.
Trushkov, I.V., Chuvylkin, N.D., Koz'min, A.S., and Zefirov, N.S., Izv. Ross. Akad. Nauk, Ser. Khim., 1995, p. 804.
Jedrzejczak, M., Motie, R.E., Satchel, D.P.N., Satchel, S.S., and Wassef, W.N., J. Chem. Soc., Perkin Trans. 2, 1994, p. 1471.
Williams, A., Concerted Organic and Bio-Organic Mechanisms, Florida: CRC, 2000.
Carroll, F.A., Perspectives on Structure and Mechanism in Organic Chemistry, California: ITP, 1998.
Pross, A., J. Org. Chem., 1984, vol. 49, p. 1811.
Masel, R.I., Chemical Kinetics and Catalysis, New York: Wiley, 2001.
Rybachenko, V.I., Schroeder, G., Chotii, K.Yu., and Kovalenko, V.V., Teor. Eksp Khim., 1998, vol. 34, p. 96.
Rybachenko, V.I., Schroeder, G., Chotii, K.Yu., Titov, E.V., Grebenyuk, L.V., Lenska, B., and Kovalenko, V.V., Russ. J. Gen. Chem., 2001, vol. 71, p. 1608.
Zhong, M. and Brauman, J.I., J. Am. Chem. Soc., 1999, vol. 121, p. 2508.
Lee, I., Lee, D., and Kim, C.K., J. Phys. Chem. A, 1997, vol. 101, p. 879; Wilbur, J.L. and Brauman, J.I., J. Am. Chem. Soc., 1994, vol. 116, p. 5839.
Savelova, V.A., Solomoichenko, T.N., Ved', T.V., Sadovskii, Yu.S., and Simanenko, Yu.S., Zh. Org. Khim., 1993, vol. 29, p. 666.
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Rybachenko, V.I., Schroeder, G., Chotii, K.Y. et al. Reaction of Acetyl and Benzoyl Chlorides with Pyridines and Pyridine N-Oxides. Russian Journal of Organic Chemistry 40, 412–416 (2004). https://doi.org/10.1023/B:RUJO.0000034981.44740.a5
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DOI: https://doi.org/10.1023/B:RUJO.0000034981.44740.a5