Abstract
It was established by PMR spectral data that in solutions of derivatives of 5-acetoxymethyl-, 5-methyl-, and 5-hydroxymethyl-2,2-dimethyl-1,3-dioxanes with nitrogen-containing substituents (2,4-disubstituted 1,3,5-triazin-6-ylamino, benzamido, and nitro groups) with an N-C(5) bond the 1,3-dioxane ring exists in the chair conformation with primarily an axial orientation of the nitrogen-containing substituent. Depending on the nature of the substituents attached to the C(5) atom, the 1,3-dioxane ring may exist either in the stable chair conformation or may undergo rapid inversion of the chair-chair type at 20 °C.
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A. L. Remizov, B. O. Kraiz, A. I. Kol'tsov, and V. I. Alekseev, Zh. Obshch. Khim., 42, 1799 (1977).
B. O. Kraiz and A. L. Remizov, Khim.-farm. Zh., No. 1, 45 (1981).
L. K. Yuldasheva and R. P. Arshinova, Teor. Eksp. Khim., 3, 641 (1967).
A. V. Bogat-skii, Yu. Yu. Samitov, and Z. D. Bogat-skaya, Zh. Org, Khim., 5, 2230 (1969).
Yu. Yu. Samitov, G. I. Goryashin, A. V. Bogat-skii, and O. S. Stepanova, Khim. Geterotsikl. Soedin., No. 5, 614 (1968).
M. Anteunis, D. Tavernier, and F. Borremants, Heterocycles, 4, 293 (1976).
A. L. Remizov, B. O. Kraiz, and A. S. Petrov, Zh. Obshch. Khim., 40, 1616 (1970).
T. Urbanski, Zh. Vsesoyuzn. Khim. Obshchestva, 7, 396 (1962).
S. Malinowski and T. Urbanski, Roczn. Chem., 25, 183 (1951).
B. O. Kraiz and A. L. Remizov, Zh. Org. Khim., 15, 1282 (1979).
T. Urbanski, Roczn. Chem., 31, 37 (1957).
M. Senkus, J. Am. Chem. Soc., 65, 1656, (1943).
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The author sincerely thanks A. I. Kol'tsov for his assistance in recording and interpreting the PMR spectra.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 468–473, April, 1985.
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Kraiz, B.O. Conformation of 5,5-disubstituted 2,2-dimethyl-1,3-dioxanes. Chem Heterocycl Compd 21, 387–392 (1985). https://doi.org/10.1007/BF00504395
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DOI: https://doi.org/10.1007/BF00504395