Abstract
The structure of 5,5-bis(bromomethyl)-2-methyl-2-phenyl-1,3-dioxane 1 has been studied by means of 1H and 13C NMR spectroscopy as well as X-ray diffraction analysis. The molecules of compound 1 exist in the chair conformation with the axially oriented phenyl group. The computer simulation using DFT approximation at the PBE/3ξ level has revealed the route of interconversion of the ring and the optimal conformation of the phenyl group corresponding to the data of X-ray diffraction analysis.
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References
Internal Rotation in Molecules, Orville-Thomas, W.J., Ed., Wiley-Interscience, 1974.
Kuznetsov, V.V., Russ. Chem. Bull. Int. Ed., 2005, vol. 54, no. 7, p. 1543. doi 10.1007/s11172-006-0001-0
Khazhiev Sh.Yu., Khusainov, M.A., Khalikov, R.A., Tyumkina, T.V., Meshcheryakova, E.S., Khalilov, L.M., and Kuznetsov, V.V., Russ. J. Gen. Chem., 2018, vol. 88, no. 3, p. 397. doi 10.1134/S1070363218030040
Kuznetsov, V.V., Russ. J. Org. Chem., 2014, vol. 50, no. 9, p. 1227. doi 10.1134/S1070428014090012
Kurmaeva, E.S., Chalova, O.B., Chistoedova, G.I., Lapuka, L.F., Kiladze, T.K., Kantor, E.A., and Rakhmankulov, D.L., Zh. Org. Khim., 1985, vol. 21, no. 1, p. 131.
Bochkor, S.A., Lapuka, L.F., Kurmaeva, E.S., Chalova, O.B., Zlotskii, S.S., and Rakhmankulov, D.L., Chem. Heterocycl. Compd., 1987, vol. 23, no. 5, p. 500. doi 10.1007/BF00476374
Khazhiev Sh.Yu., Khusainov, M.A., and Kantor, E.A., Russ. J. Org. Chem., 2011, vol. 47, no. 3, p. 450. doi 10.1134/S1070428011030225
Khazhiev Sh.Yu. and Khusainov, M.A., Russ. J. Org. Chem., 2017, vol. 53, no. 5, p. 717. doi 10.1134/S1070428017050116
Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., 2005, vol. 54, no. 3, p. 820. doi 10.1007/s11172-005-0329-x
Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, no. 1, p. 112. doi 10.1107/S0108767307043930
HyperChem 8.0. http://www.hyper.com.
Rakhmankulov, D.L., Syrkin, A.M., Karakhanov, R.A., Kantor, E.A., Zlotskii, S.S., and Imashev, U.B., Fizikokhimicheskie svoistva 1,3-dioksanov (Physico-Chemical Properties of 1,3-Dioxanes), Moscow: Khimiya, 1980.
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Russian Text © Sh.Yu. Khazhiev, M.A. Khusainov, R.A. Khalikov, T.V. Tyumkina, E.S. Meshcheryakova, L.M. Khalilov, V.V. Kuznetsov, 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 2, pp. 197–201.
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Khazhiev, S.Y., Khusainov, M.A., Khalikov, R.A. et al. Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2-methyl-2-phenyl-1,3-dioxane. Russ J Gen Chem 89, 199–203 (2019). https://doi.org/10.1134/S1070363219020051
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DOI: https://doi.org/10.1134/S1070363219020051