Abstract
2-Arylidene-3-oxoquinuclidine oximes were obtained from the products of condensation of 3-oxoquinuclidine with aromatic aldehydes. It is shown that three of the four theoretically possible isomers (isomerism involving the C=C and C=N bonds) are formed; their thermal stability was studied. The structures of the isomeric oximes was established on the basis of data from the 1H and 13C NMR spectra and were confirmed by data from chromatographic mass spectrometry and the UV and IR spectra.
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G. R. Clemo and E. Hoggarth, J. Chem. Soc., 1241 (1939).
E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974).
E. J. Warawa, N. J. Mueller, and R. Jules, J. Med. Chem., 17, 497 (1974).
L. N. Yakhontov, L. I. Mastafanova, K. F. Turchin, Yu. N. Sheinker, and M. V. Rubtsov, Dokl. Akad. Nauk SSSR, 168, 1085 (1966).
E. E. Mikhlina, V. Ya. Vorob'eva, K. F. Turchin, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., 1083 (1968).
I. Morishima, K. Okada, T. Yonezawa, and K. Goto, J. Am. Chem. Soc., 93, 3922 (1971).
L. Levy and G. L. Nelson, J. Am. Chem. Soc., 94, 4897 (1972).
D. Hadzi and L. Premru, Spectrochim. Acta, 23A, 35 (1967).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 666–674, May, 1981.
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Filipenko, T.Y., Gorbyleva, O.I., Turchin, K.F. et al. Synthesis and three-dimensional structure of 2-arylidene-3-oxoquinuclidine oximes. Chem Heterocycl Compd 17, 490–497 (1981). https://doi.org/10.1007/BF00505697
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DOI: https://doi.org/10.1007/BF00505697