Skip to main content
Log in

Stereospecificity of spin-spin coupling constants (SSCC) of 1H, 15N, and 19F nuclei in substituted 2,2-bis(trifluoromethyl)aziridines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1-Chloro-, 3-methyl-, 1-chloro-3-cyano-, 1-carbomethoxymethoxy-3-methyl-, and 1-carboxymethoxy-3-methyl-2,2-bis(trifluoromethyl)aziridines were synthesized for the first time. Criteria for distinguishing cis- and trans-3-substituted and 1,3-disubstituted 2,2-bis(trifluoromethyl)aziridines from the parameters of the 1H, 13C, and 19F NMR spectra were found.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. R. G. Kostyanovskii, G. K. Kadorkina, S. V. Varlamov, I. I. Chervin, and I. K. A. Romero Maldonado, Khim. Geterotsikl. Soedin., No. 4, 472 (1988).

    Google Scholar 

  2. R. G. Kostyanovskii, G. K. Kadorkina, and K. S. Zakharov, Dokl. Akad. Nauk SSSR, 221, 126 (1975).

    Google Scholar 

  3. R. G. Kostyanovskii, G. K. Kadorkina, G. V. Shustov, and K. S. Zakharova, Dokl. Akad. Nauk SSSR, 221, 370 (1975).

    Google Scholar 

  4. R. Wasylishen and T. Schaefer, Can. J. Chem., 50, 2989 (1972).

    Google Scholar 

  5. A. A. Fomichev and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR, 199, 1110 (1971).

    Google Scholar 

  6. A. Nakanishi and O. Yamamoto, Tetrahedron, 30, 2115 (1974).

    Google Scholar 

  7. R. G. Kostyanovskii (Kostyanovsky), I. I. Chervin, A. A. Fomichev, Z. E. Samoilova, (Samojlova), K. N. Makarov, Yu. V. Zeifman, and B. L. D'yatkin (Dyatkin), Tetrahedron Lett., No. 46, 4021 (1969).

    Google Scholar 

  8. S. J. Brois, Trans. N.Y. Acad. Sci., 31, 931 (1969).

    Google Scholar 

  9. K. D. Gundermann, K. Buzzin, F. J. Sprender, and H. Schulze, Chem. Ber., 105, 312 (1972).

    Google Scholar 

  10. D. Höfner, J. Tamir, and G. Brinsch, Org. Magn. Reson., 11, 172 (1978).

    Google Scholar 

  11. R. G. Kostyanovskii, G. K. Kadorkina, and A. P. Pleshkova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1187 (1976).

    Google Scholar 

  12. R. G. Kostyanovskii, G. K. Kadorkina, G. V. Shustov, I. I. Chervin, and Sh. S. Nasibov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 145 (1982).

    Google Scholar 

  13. P. Scheiner, J. Am. Chem. Soc., 90, 488 (1968).

    Google Scholar 

  14. J. Bourgois, M. Bourgois, and F. Texier, Bull. Soc. Chim. France, Nos. 9/10, 485 (1978).

    Google Scholar 

  15. K. Burger and E. Burgis, Annalen., 741, 39 (1970).

    Google Scholar 

  16. R. G. Kostyanovskii, A. I. Mishchenko, A. V. Prosyanik, and N. L. Zaichenko, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1572 (1983).

    Google Scholar 

  17. R. G. Kostyanovskii, G. K. Kadorkina, I. I. Chervin, Sh. S. Nasibov, and I. K. A. Romero Maldonado, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 376 (1985).

    Google Scholar 

  18. R. G. Kostyanovskii, G. K. Kadorkina, A. B. Zolotoi, O. A. D'yachenko, L. O. Atovmyan, I. I. Chervin, and Sh. S. Nasibov, Dokl. Akad. Nauk SSSR, 267, 1103 (1983).

    Google Scholar 

  19. V. F. Snegirev, M. V. Galakhov, V. A. Petrov, K. N. Makarov, and V. I. Bakhmutov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1318 (1986).

    Google Scholar 

  20. I. L. Knunyants and Yu. V. Zeifman, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 711 (1967).

    Google Scholar 

  21. G. V. Shustov, A. B. Zolotoi, N. L. Zaichenko (Zaitchenko), O. A. D'yachenko (Dyachenko), L. O. Atovmyan, and R. G. Kostyanovskii (Kostyanovsky), Tetrahedron, 40, 2151 (1984).

    Google Scholar 

  22. R. G. Kostyanovskii (Kostyanovsky), V. I. Markov, and I. M. Gella, Tetrahedron Lett., No. 14, 1301 (1972).

    Google Scholar 

  23. Yu. Minoura, M. Takebajashi, and C. C. Price, J. Am. Chem. Soc., 81, 4989 (1959).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Communication 64 from the series “Asymmetric nitrogen.” See [1] for communication 63.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 757–765, June, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kostyanovskii, R.G., Kadorkina, G.K., Chervin, I.I. et al. Stereospecificity of spin-spin coupling constants (SSCC) of 1H, 15N, and 19F nuclei in substituted 2,2-bis(trifluoromethyl)aziridines. Chem Heterocycl Compd 24, 616–624 (1988). https://doi.org/10.1007/BF00475594

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475594

Keywords

Navigation