Abstract
The reaction of trifluoromethyl-containing enones with hydroxylamine under various conditions is studied. The products in basic medium are equilibrating mixtures of isoxazolidine diastereomers in an ∼1∶1 ratio. The energy of the nitrogen atom inversion barrier in these compounds is 50–60 kJ/mol. Broadened signals are observed at room temperature in the1H and13C NMR.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
R. L. Elliot, H. Kopecka, N.-H. Lin, Y. He, and D. S. Garvey,Synthesis, No. 7, 772 (1995).
A. A. Akhrem, F. A. Lakhvich, and V. A. Khripach,Khim. Geterotsikl. Soedin., No. 9, 1155 (1981).
F. A. Lakhvich, E. V. Koroleva, and A. A. Akhrem,Khim. Geterotsikl. Soedin., No. 4, 435 (1989).
N. Isikawa, T. Abe, S. Nagase, H. Koayashi, S. Nakagawa, S. Kawachi, S. Munekata, K. Tamura, H. Wada et al.,Preparation and Functions of Fluorine Compounds, CMC Col. Ltd., Tokyo (1987).
L. M. Yagupol'skii,Aromatic and Heterocyclic Compound with Fluorine-Containing Substituents [in Russian], Naukova Dumka, Kiev (1988), 320 pp.
K. I. Pashkevich, V. I. Saloutin, and I. Ya. Postovskii,Uspekh. Khim.,50, 325 (1981).
A. Colla, M. A. P. Martins, G. Clar, S. Krimmer, and P. Fisher,Synthesis, No. 6, 483 (1991).
I. I. Gerus, M. G. Gorbunova, S. I. Vdovenko, Yu. L. Yagupol'skii, and V. P. Kukhar',Zh. Org. Khim.,26, 1877 (1990).
M. A. P. Martins, A. F. C. Flores, R. Freitag, and N. Zanatta,J. Heterocycl. Chem.,32, 731 (1995).
O. A. Kuznetsova, V. I. Filyakova, and K. I. Pashkevich,Izv. Ross. Akad. Nauk, Ser. Khim., No. 5, 1306 (1996).
R. J. Linderman and K. S. Kirollos,Tetrahedron Lett.,30, 2049 (1989).
K. Tanaka, H. Masuda, and K. Mitsuhashi,Bull. Chem. Soc. Jpn.,57, 2184 (1984).
W. J. Middleton,J. Org. Chem.,49, 919 (1984).
D. P. Del'tsova, E. S. Ananyan, and N. P. Gambaryan,Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 362 (1971).
H. Tsuge, T. Okano, S. Eguchi, and H. Kimoto,J. Chem. Soc. Perkin Trans. I, No. 10, 1581 (1997).
T. M. Chau, C. Beaute, S. Cornuel, and N. Thoai,Tetrahedron Lett., No. 45, 4313 (1971).
C. Kashima, N. Yoshiwara, S. Shirai, and Y. Omote,Chem. Lett., No. 5, 1455 (1982).
M. L. Parkayastha, L. Bhat, H. Ila, and H. Junjappa,Synthesis, No. 6, 631 (1995).
M. Shamim Akhtar, M. Seth, and A. P. Bhaduri,Indian J. Chem., Sect. B.,26B, 71, (1987).
C. Kashima, S. Shirai, N. Yoshiwara, and Y. Omote,J. Chem. Soc. Chem. Commun., No. 17, 826 (1980).
V. G. Nenaidenko, A. V. Sanin, and E. S. Balenkova,Zh. Org. Khim.,31, 786 (1995).
R. G. Kostyanovsky and V. F. Rudchenko,Dokl. Akad. Nauk SSSR,263, 897 (1982).
R. G. Kostyanovsky, V. F. Rudchenko, O. A. D'yachenko, I. I. Chervin, A. B. Zolotoi, and L. O. Atovmyan,Tetrahedron,35, 213 (1979).
V. Ya. Sosnovskikh, M. Yu. Mel'nikov, and V. A. Kutsenko,Izv. Ross. Akad. Nauk, Ser. Khim., No. 8, 1553 (1997).
V. Ya. Sosnovskikh, M. Yu. Mel'nikov, and V. A. Kutsenko,Izv. Ross. Akad. Nauk, Ser. Khim., No. 7, 1866 (1996).
V. G. Nenaidenko, A. V. Sanin, V. S. Kuz'min, and E. S. Balenkova,Zh. Org. Khim.,32, 1579 (1996).
V. G. Nenaidenko and E. S. Balenkova,Zh. Org. Khim.,28, 600 (1992).
V. G. Nenajdenko, I. D. Gridnev, and E. S. Balenkova,Tetrahedron,50, 11023 (1994).
M. G. Gorbunova, I. I. Gerus, and V. P. Kukhar,J. Fluor. Chem.,65, 25 (1993).
A. V. Sanin, V. G. Nenajdenko, K. I. Smolko, D. I. Denisenko, and E. S. Balenkova,Synthesis, No. 6, 842 (1998).
Additional information
M. V. Lomonosov Moscow State University, Moscow 119899, Russia
A. N. Nesmeyanov Institute of Elementorganic Compounds of the Russian Academy of Sciences, Moscow 117907. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 395–406, March, 1999.
Rights and permissions
About this article
Cite this article
Nenajdenko, V.G., Sanin, A.V., Tok, O.L. et al. Synthesis and stereochemistry of trifluoromethyl-containing isoxazolidines. Chem Heterocycl Compd 35, 348–357 (1999). https://doi.org/10.1007/BF02259367
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02259367