Conclusions
-
1.
The vinyl ethers of pyridine and quinoline exist preferentially in the nonplanar Strans conformation.
-
2.
In the vinyl esters of pyridine and quinoline the p-Π conjugation is concurrent in nature and depends on the position of the vinyloxy group in the heterocycle.
Similar content being viewed by others
Literature cited
B. A. Trofimov, Heteroatomic Derivatives of Acetylene [in Russian], Nauka, Moscow (1981), pp. 205–226.
N. J. Koole, M. J. A. Bie, and P. E. Hansen, Org. Magn. Reson.,22, 146 (1984).
G. A. Kalabin and L. B. Krivdin, Zh. Org. Khim.,1985, 1137.
E. S. Hand and W. W. Paulder, Org. Magn. Reson.,14, 52 (1980).
A. Gordon and R. Ford, Chemist's Companion, Wiley-Interscience (1976).
H. Günther, NMR Spectroscopy. An Introduction, Wiley (1984).
T. M. Spotswood and C. J. Tanzer, Aust. J. Chem.,20, 1227 (1967).
R. Houssin and J. P. Henichart, Org. Magn. Reson.,16, 202 (1981).
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).
W. C. Davidon, Compt. J.,10, 406 (1968).
E. Taskinen, Tetrahedron,34, 433 (1978).
J. A. Su, E. Siew, E. V. Brown, and S. L. Smith, Org. Magn. Reson.,11, 565 (1978).
A. M. Kook, S. L. Smith, and E. V. Brown, Org. Magn. Reson.,22, 730 (1984).
Z. V. Stepanova, G. G. Skvortsova, M. A. Andriyankov, and D. G. Kim, Second Symposium on the Chemistry and Technology of Heterocyclic Compounds from Fossil Fuels. Abstracts [in Russian], Donetsk (1973), p. 40.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR. Seriya Khimicheskaya, No. 2, pp. 317–323, February, 1987.
Rights and permissions
About this article
Cite this article
Afonin, A.V., Voronov, V.K., Andriankov, M.A. et al. Structure of pyridine and quinoline vinyl ethers according to data from1H and13C NMR spectra and quantum-chemical calculations. Russ Chem Bull 36, 279–284 (1987). https://doi.org/10.1007/BF00959363
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00959363