Abstract
By means of 1H NMR spectroscopy isomerism was demonstrated in N-alkyl substituted 5-chloromethyl-1,3-oxazolidines due to relative cis-trans orientation of substituents in 2 and 5 positions of the ring. The preferred configuration in 2,3-diaryl-5-chloromethyl-1,3-oxazolidines, cis-(2R,5R), was proved by quantum-chemical calculations.
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REFERENCES
Rakhmankulov, D.L., Latypova, F.N., and Zlotskii, S.S., Sintez i biologicheskaya aktivnost' 1,3-digeterotsikloalkanov (Synthesis and Biolocal Activity of 1,3-Diheterocycloalkanes), Moscow: NIITEKhim., 1985.
Rakhmankulov, D.L., Zorin, V.V., Latypova, F.N., Musavirov, R.S., and Siraeva, I.N., Metody sinteza 1,3-digeteroanalogov tsikloalkanov (Methods of Synthesis of 1,3-Diheterocycloalkanes), Ufa: GINTL “Reaktiv”, Nova Science Publ., 1998.
Rakhmankulov, D.L., Karakhanov, R.A., Zlotskii, S.S., Kantor, E.A., Imashev, U.B., and Syrkin, A.M., Itogi Nauki i Tekhniki, Ser. Tekhnol. Organ. Veshchestv, Moscow: VINITI, 1979, vol. 5, p. 287.
Rakhmankulov, D.L., Zorin, V.V., Kuramshin, E.M., and Zlotskii, S.S., Konstanty skorosti gomoliticheskikh zhidkofaznykh reaktsii 1,3-digeteroanalogov tsikloalkanov i rodstvennykh soedinenii (Rate Constants of Homolytic Reactions in the Liquid Phase for 1,3-Diheteroanalogs of Cycloalkanes and Their Derivatives), Ufa: GINTL “Reaktiv”, 1999.
Rakhmankulov, D.L., Zorin, V.V., Kuramshin, E.M., Zlotskii, S.S., Zorina, L.N., Sergeeva, L.G., and Sherepovets, V.V., Metody issledovaniya reaktsionnoi sposobnosti organicheskikh soedinenii (Methods of Investigation of Reactivity of Organic Compounds), Ufa: GINTL “Reaktiv”, 1999.
Bulatova, O.F., Romanov, N.A., Chalova, O.B., and Rakhmankulov, D.L., Zh. Org. Khim., 1994, vol. 30, no. 1, pp. 55–58.
Kirby, A., Anomeric Effect and Related Stereoelectronic Effects in Oxygen, Springer Verlag, 1982.
Potapov, V.M., Stereokhimiya (Stereochemistry), Moscow: Khimiya, 1976.
Deslongchamps, P., Stereoelectronic Effects in Organic Chemistry, Pergamon Press, 1983, 375 p.
Crabb, T., Hall, M., and Willimans, R., Tetrahedron, 1973, vol. 29, pp. 3389–3398.
Alimirzoev, F.A., Lapshova, A.A., Zorin, V.V., Stepanyants, A.U., Lezina, V.P., Lapotova, F.N., Zlotskii, S.S., and Rakhmankulov, D.L., Zh. Prikl. Khim., 1980, vol. 53, no. 4, pp. 911–914.
Just, G., Potvin, P., Uggowitzer, P., and Bird, P., J. Org. Chem., 1983, vol. 48, pp. 2923–2924.
Beckett, A. and Jones, G., Tetrahedron, 1977, vol. 33, no. 24, pp. 3313–3316.
Irivin, W.J. and Wheeler, D.L., J. Chem. Soc. C 1971, vol. 19, pp. 3166–3167.
Tarahasku, A., Suzuki, Y., and Kametani, T., Heterocycles, 1983, vol. 20, no. 4, pp. 607–610.
Agami, C. and Rizk, T., Tetrahedron, 1985, vol. 41, no. 3, pp. 537–540.
Rakhmankulov, D.L., Chalova, O.B., Kiladze, T.K., and Kantorm E.A., Khim. Geterotsikl. Soed., 1984, no. 3, pp. 291–306.
Gunther, H., NMR Spectroscopy, Chichester: Wiley.
Winter, J., Davis, A., and Saunders, M., J. Comput. Aided Molecular Design I, 1987, pp. 31–51.
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Bulatova, O.F., Chalova, O.B. & Rakhmankulov, D.L. Structure of Substituted 5-Chloromethyloxazolidines. Russian Journal of Organic Chemistry 37, 1753–1756 (2001). https://doi.org/10.1023/A:1013934320612
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DOI: https://doi.org/10.1023/A:1013934320612