Skip to main content
SpringerLink
Log in

Regioselective synthesis of new functionally substituted tetrazolium salts

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The 1,4-, 1,3-di- and 1,3,5-trisubstituted tetrazolium salts were obtained regioselectively and with high yields by the quaternization of 1- and 2-monosubstituted and 1,5-disubstituted tetrazoles with diacetone alcohol in perchloric acid. An X-ray crystallographic analysis of 1-(2-methylpentan-4-on-2-yl)-4-methyltetrazolium perchlorate was undertaken.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. R. N. Butler,Comprehensive Organic Chemistry (Ed. A. R. Katritzky, C. W. Rees, and E. F. V. Scriven), Vol. 4, Pergamon Press, Oxford (1996), p. 621.

    Google Scholar 

  2. V. V. Semenov, V. S. Bogdanov, B. S. Él'yanov, L. G. Mel'nikova, S. A. Shevelev, V. M. Zhulin, and A. A. Fainzil'berg,Khim. Geterotsikl. Soedin., No. 8, 1118 (1982).

    Google Scholar 

  3. D. Moderhack and D.-O. Bode,J. Chem. Soc. Perkin Trans. I, 1483 (1992).

  4. P. N. Gaponik, Yu. V. Grigor'ev, T. N. Andreeva, and I. I. Maruda,Khim. Geterotsikl. Soedin., No. 7, 915 (1995).

    Google Scholar 

  5. P. N. Gaponik, S. V. Voitekhovich, O. A. Ivashkevich, A. S. Lyakhov, and A. A. GovorovaKhim. Geterotsikl. Soedin., No. 5, 657 (1998).

    Google Scholar 

  6. V. V. Saraev and E. L. Golod,Zh. Org. Khim., 33, 629 (1997).

    Google Scholar 

  7. V. I. Boev, E. M. Krasnikov, A. I. Mokalenko, E. I. Pil'ko, L. V. Snegur, V. N. Babin, and Yu. S. Nekrasov,Zh. Obshch. Khim., 67, 1386 (1997).

    Google Scholar 

  8. P. N. Gaponik, S. V. Voitekhovich, I. I. Maruda, A. A. Kulak, and O. A. Ivashkevich, Polish J. Chem., 72, 2247 (1998).

    Google Scholar 

  9. Y. K. Kim and J. D. Hatfield,J. Chem. Eng. Data, 30, 149 (1985).

    Google Scholar 

  10. N. C. Deno, H. C. Richey, N. Friedmann, J. J. Hodye, and C. U. Pittman, Jr.,J. Am. Chem. Soc., 85, 2991 (1963).

    Google Scholar 

  11. A. O. Koren' and P. N. Gaponik,Khim. Geterotsikl. Soedin., No. 12, 1643 (1990).

    Google Scholar 

  12. P. N. Gaponik and S. V. Voitekhovich,Zh. Org. Khim., 34, 788 (1998).

    Google Scholar 

  13. P. N. Gaponik, O. A. Ivashkevich, V. N. Naumenko, T. B. Kovalyova, T. N. Andreeva, and O. A. Koren,Spectrochim. Acta, 49A, 135 (1993).

    Google Scholar 

  14. D. M. Zimmerman and R. A. Olofson,Tetrahedron Lett., No. 39, 3453 (1970).

    Google Scholar 

  15. S. Vinogradov,Molecular Interactions (Eds. G. Rataichak and U. Orville-Thomas) [Russian translation], Mir, Moscow (1988), p. 184.

    Google Scholar 

  16. P. N. Gaponik, V. P. Karavai, and Yu. V. Grigor'ev,Khim. Geterotsikl. Soedin., No. 11, 1521 (1985).

    Google Scholar 

  17. P. N. Gaponik, V. P. Karavai, and N. I. Chernavina,Vestnik Belorus. Univ., Ser. 2, No. 2, 23 (1983).

    Google Scholar 

  18. G. M. Sheldrick,Program for Crystal Structure Refinement, Univ. Goettingen (1997).

  19. G. M. Sheldrick,Acta Crystallogr., A46, 467 (1990).

    Google Scholar 

  20. G. M. Sheldrick, Z. Dauter, K. S. Wilson, H. Hope, and L. Sieker,Acta Crystallogr., D49, 18 (1993).

    Google Scholar 

Download references

Authors
  1. P. N. Gaponik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Voitekhovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. S. Lyakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. I. Maruda
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Scientific-Research Institute of Physicochemical Problems, Belorus State University, Minsk; e-mail: fhp@fhp.bsu.unibel.by. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1222–1229, September, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gaponik, P.N., Voitekhovich, S.V., Lyakhov, A.S. et al. Regioselective synthesis of new functionally substituted tetrazolium salts. Chem Heterocycl Compd 35, 1078–1084 (1999). https://doi.org/10.1007/BF02251800

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02251800

Keywords

Search

Navigation