Abstract
Study of the mechanism of formation of 1,3-oxazinane in the reaction of α-methylstyrene with formaldehyde and amines in aqueous medium has shown that 3,6-dimethyl-6-phenyl-1,3-oxazinane is formed as a result of transformations of 4-methyl-4-phenyl-1,3-dioxane which is the Prins reaction product.
References
Fattakhov, A.Kh., Talipov, R.F., Kayumova, A.F., and Shepelevich, I.S., Vestn. Bashk. Univ. 2016, vol. 21, p. 893.
Hennion, G., Price, C., and Wolff, V., J. Am. Chem. Soc., 1955, vol. 77, p. 4633.
Schmidle, C.J. and Mansfield, R.C., J. Am. Chem. Soc., 1955, vol. 77, p. 4636.
Cohen, T. and Onopchenko, A., J. Org. Chem., 1983, vol. 48, p. 4531.
Hartough, H.D., Dickert, J.J., and Meisel, S.L., US Patent no. 2 647 117, 1953; Chem. Abstr., 1954, vol. 48, p. 8265.
Rocha, G.B., Freire, R.O., Simas, A.M., and Stewart, J.J.P., J. Comput. Chem., 2006, vol. 27, p. 1101.
Rezac, J. and Hobza, P.. J. Chem. Theory Comput., 2012, vol. 8, p. 141.
Dewar, M.J.S., Zoebisch, E.G., Healy, E.F., and Stewart, J.J.P., J. Am. Chem. Soc., 1985, vol. 107, p. 3902.
Kupova, O.Y., Vakulin, I.V., and Talipov, R.F., Comput. Theor. Chem. 2013, vol. 1013, p. 57.
Zhang, J., Hua, L., Li, F., Wu, X., Tian, S., and Yang, J., Synth. Commun. 2012, vol. 42, p. 1234.
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Original Russian Text © A.Kh. Fattakhov, R.F. Talipov, G.R. Talipova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 12, pp. 1836–1838.
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Fattakhov, A.K., Talipov, R.F. & Talipova, G.R. Role of Prins Reaction and Aminomethylation in the Synthesis of 1,3-Oxazinane from α-Methylstyrene. Russ J Org Chem 54, 1851–1853 (2018). https://doi.org/10.1134/S1070428018120229
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DOI: https://doi.org/10.1134/S1070428018120229