Abstract
The configuration and conformations of stereoisomeric 4R-8-(3,4-dihydro-2-pyranyloxy)quinolines were studied by means of their PMR spectra. It was established that the trans isomers of the investigated compounds have primarily a “half-chair” conformation and display an anomeric effect. A “sofa” conformation is proposed for the labile cis isomers.
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G. G. Skvortsova, M. A. Andriyankov, Z. V. Stepanova, T. V. Kashik, S. M. Ponomareva, and L. D. Kim., Khim. Geterotsikl. Soedin., No. 3, 375 (1976).
N. S. Zefirov and N. M. Shekhtman, Usp. Khim., 40, 593 (1971).
N. M. Shekhtman, E. A. Viktorova, É. A. Karakhanov, N. N. Khvorostukhina, and N. S. Zefirov, Dokl. Akad. Nauk SSSR, 196, 367 (1970).
G. Descotes, J. C. Martin, and N. Mathicolonis, Bull. Soc. Chim. France, 1077 (1972).
M. Karplus, J. Am. Chem. Soc., 85, 1899 (1963).
D. J. Collins, J. J. Hobbs, and S. Sternhell, Austral. J. Chem., 16, 1030 (1963).
M. Barfield and B. Chakrabarti, Chem. Rev., 69, 757 (1969).
N. S. Zefirov, N. M. Shekhtman, and É. A. Karakhanov, Zh. Organ. Khim., 3, 1925 (1967).
E. W. Garbish, J. Am. Chem. Soc., 36, 5561 (1964).
V. F. Bystrov, Usp. Khim., 41, 512 (1972).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 607–610, May, 1976.
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Sigalov, M.V., Voronov, V.K., Andriyankov, M.A. et al. Aryloxydihydropyrans. XII. Configuration and conformations of 8-(3,4-dihydro-2-pyranyloxy)quinoline derivatives. Chem Heterocycl Compd 12, 508–511 (1976). https://doi.org/10.1007/BF00470100
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DOI: https://doi.org/10.1007/BF00470100