Abstract
Ketone oxime O-vinyl ethers having alkyl or phenyl radicals react with trifluoroacetic anhydride in ether in the presence of pyridine, yielding 43-54% of the corresponding ketone oxime O-(trans-4,4,4-trifluoro-3-oxo-1-butenyl) ethers with high stereoselectivity.
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REFERENCES
Hojo, M., Masuda, R., Kokuryo, Y., Shioda, H., and Matsuo, S., Chem. Lett., 1976, pp. 499-502.
Hojo, M., Masuda, R., and Okada, E., Synthesis, 1989, no. 3, pp. 215-217.
Hojo, M., Masuda, R., and Okada, E., Synthesis, 1990, no. 4, pp. 347-350.
Gorlov, D.V., Kurykin, M.A., and Petrova, O.E., Izv. Ross. Akad. Nauk, Ser. Khim., 1999, no. 9, pp. 1813-1814.
Tarasova, O.A., Korostova, S.E., Mikhaleva, A.I., Sobenina, L.N., Nesterenko, R.N., Shevchenko, S.G., and Trofimov, B.A., Zh. Org. Khim., 1994, vol. 30, no. 6, pp. 810-815.
Trofimov, B.A., Mikhaleva, A.I., Vasil'tsov, A.M., Schmidt, E.Yu., Tarasova, O.A., Morozova, L.V., Sobenina, L.N., Preiss, T., and Henkelmann, J., Synthesis, 2000, no. 8, pp. 1125-1132.
Trofimov, B.A., Schmidt, E.Yu., Mikhaleva, A.I., Vasil'tsov, A.M., Larina, L.I., and Klyba, L.V., Mendeleev Commun., 1999, no. 6, pp. 238-239.
Sohlberg, K., Leary, S.P., Owen, N.L., and Trofimov, B.A., Vibrat. Spectrosc., 1997, vol. 13, pp. 227-234.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Jr., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., and Pople, J.A., Gaussian 98. Revision A.6, Pittsburgh PA: Gaussian, 1998.
Chemical Applications of Spectroscopy, West, W., Ed., New York: Intersci., 1956. Translated under the title Primenenie spektroskopii v khimii), Moscow: Inostrannaya Literatura, 1959, p. 428.
Smith, P.A.S., The Chemistry of Open-Chain Organic Nitrogen Compounds, New York: Benjamin, 1966, ch. VII, p. 100.
Afonin, A.V., Ushakov, I.A., Tarasova, O.A., Shmidt, E.Yu., Mikhaleva, A.I., and Voronov, V.K., Russ. J. Org. Chem., 2000, vol. 36, no. 12, pp. 1777-1783.
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Vasil'tsov, A.M., Shmidt, E.Y., Mikhaleva, A.I. et al. Trifluoroacetylation of Ketone O-Vinyloximes. Russian Journal of Organic Chemistry 37, 334–338 (2001). https://doi.org/10.1023/A:1012363904621
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DOI: https://doi.org/10.1023/A:1012363904621