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1H- and 13C-NMR study of rotational isomerism in N-vinyltetrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The 1H- and 13C-NMR spectral parameters of N-vinyltetrazoles have been analyzed. It has been found that rotational isomerism is inherent to 1- and 2-vinyltetrazoles. A quantitative estimate of the ratio of rotational isomers has been made. In the case of 1-vinyltetrazoles, introduction of a substituent to the 5-position in the tetrazole ring stabilizes the trans-orientation of the vinyl group relative to the substituent, while in the case of 2-vinyltetrazoles the presence of a substituent in the 5-position of the ring essentially does not affect the conformer population.

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Literature Cited

  1. L. A. Es'kova, V. K. Voronov, E. S. Domnina, and G. G. Skvortsova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1012 (1985).

    Google Scholar 

  2. A. V. Afonin, V. K. Voronov, L. A. Es'kova, E. S. Domnina, E. V. Petrova, and O. A. Zasyadko, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 202 (1987).

    Google Scholar 

  3. A. V. Afonin, V. K. Voronov, B. V. Trzhtsinskaya, E. V. Rudakova, and V. V. Keiko, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1264 (1987).

    Google Scholar 

  4. L. I. Vereshchagin, S. R. Buzilova, T. K. Mityukova, A. G. Proidakov, V. N. Kizhnyaev, V. V. Il'ina, G. T. Sukhanov, G. A. Gareev, and A. K. Bogens, Zh. Org. Khim., 22, 1979 (1986).

    Google Scholar 

  5. G. Levy and G. Nelson, Handbook of Carbon-13 Nuclear Magnetic Resonance [Russian translation], Mir, Moscow (1975), p. 86.

    Google Scholar 

  6. B. A. Trofimov, Heteroatomic Derivatives of Acetylene [in Russian], Nauka, Moscow (1981), p. 264.

    Google Scholar 

  7. O. A. Ivashkevich, P. N. Gaponik, and V. N. Naumenko, Khim. Geterotsikl. Soedin., No. 2, 236 (1987).

    Google Scholar 

  8. A. V. Afonin, V. K. Voronov, M. A. Andriyankov, and D. K. Danovich, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 317 (1987).

    Google Scholar 

  9. R. Knorr, Tetrahedron, 37, 929 (1981).

    Google Scholar 

  10. G. K. Hamer, J. R. Peat, and W. F. Reynolds, Can. J. Chem., 51, 897 (1973).

    Google Scholar 

  11. W. F. Reynolds, J. R. Peat, and G. K. Hamer, Can. J. Chem., 52, 3415 (1974).

    Google Scholar 

  12. A. R. Engelmann and R. H. Contreras, J. Quant. Chem., 23, 1033 (1983).

    Google Scholar 

  13. P. C. Myhre, J. W. Edmonds, and J. D. Kruger, J. Am. Chem. Soc., 88, 2459 (1966).

    Google Scholar 

  14. A. V. Afonin, D. K. Danovich, V. K. Voronov, L. A. Es'kova, L. V. Baikalova, and S. R. Buzilova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 872 (1988).

    Google Scholar 

  15. A. V. Afonin, V. K. Voronov, and M. A. Andriyankov, Khim. Geterotsikl. Soedin., No. 11, 1568 (1986).

    Google Scholar 

  16. S. Castellano, H. Gunther, and S. Ebersole, J. Phys. Chem., 69, 4166 (1965).

    Google Scholar 

  17. A. P. Ebdon, T. N. Huckerly, and F. G. Thorpe, Tetrahedron Lett., No. 31, 2921 (1971).

    Google Scholar 

  18. C. Li and M. P. Sammes, J. Chem. Soc., Perkin I, No. 9, 2193 (1983).

    Google Scholar 

  19. T. M. Spootswood and C. J. Tanzer, Aust. J. Chem., 20, 1277 (1967).

    Google Scholar 

  20. B. A. Trofimov, M. V. Sigalov, V. M. Bzhezovskii, G. A. Kalabin, S. E. Korostova, A. I. Mikhaleva, and L. A. Balabanova, Khim. Geterotsikl. Soedin., No. 6, 768 (1978).

    Google Scholar 

  21. T. Schaefer, G. H. Penner, K. J. Davie, and R. Sebastian, Can. J. Chem., 63, 777 (1985).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1662–1667, December, 1989.

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Afonin, A.V., Vereshchagin, L.I., Buzilova, S.R. et al. 1H- and 13C-NMR study of rotational isomerism in N-vinyltetrazoles. Chem Heterocycl Compd 25, 1385–1389 (1989). https://doi.org/10.1007/BF00473869

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  • DOI: https://doi.org/10.1007/BF00473869

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