Abstract
It was shown by x-ray diffraction analysis and PMR spectroscopy that 1-acyl-5-hydroxy- and -5-hydrazinopyrazolidines have a conformation with an axial orientation of the functional group attached to the C(5) atom. The 1-salicylyl derivatives constitute an exception: in methanol solutions they exist in a conformation with an equatorial hydroxy group, whereas in dimethylformamide (DMF) the ring undergoes partial opening to give the corresponding β-hydrazido aldehydes.
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K. N. Zelenin, A. V. Dovgilevich, I. P. Bezhan, G. A. Golubeva, L. A. Sviridova, L. V. Pastushenkov, É. G. Gromova, T. A. Gatchina, and S. V. Pomogaibo, Khim. Geterotsikl. Soedin., No. 5, 659 (1984).
I. P. Bezhan, K. N. Zelenin, and V. V. Pinson, Zh. Org. Khim., 27, 493 (1982).
B. Fuchs, “Conformations of five-membered rings,” in: Topics in Stereochemistry, E. L. Eliel and N. L. Allinger, eds., Vol. 10, Wiley, New York (1978), p. 1.
N. S. Zefirov and N. M. Shekhtman, Usp. Khim., 40, 593 (1971).
A. J. Kirby, The Anomeric Effects and Related Stereoelectronic Effects at Oxygen, Springer-Verlag, Berlin (1983), p. 149.
S. F. Nelson and J. M. Buschek, J. Am. Chem. Soc., 96, 6982 (1974).
S. F. Nelson and J. M. Buschek, J. Am. Chem. Soc., 96, 6987 (1974).
K. N. Zelenin, A. V. Dovgilevich, and I. P. Bezhan, Khim. Geterotsikl. Soedin., No. 10, 1422 (1983).
M. C. E. Carron, A. F. Jullien, M. Peron, and N. Y. M. H. Letterob, French Patent No. 1,336,069; Chem. Abstr., 60, 2865d (1964).
R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya, 28, 1029 (1983).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1242–1247, September, 1985.
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Dovgilevich, A.V., Zelenin, K.N., Espenbetov, A.A. et al. Three-dimensional structures of 1-acyl-5-hydroxypyrazolidines. Chem Heterocycl Compd 21, 1034–1039 (1985). https://doi.org/10.1007/BF00515031
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DOI: https://doi.org/10.1007/BF00515031