Skip to main content
SpringerLink
Log in

Azirinium ylides from alkoxycarbonylcarbenoids and 2H-azirines: Generation and transformations

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Dirhodium tetraacetate-catalyzed decomposition of diazo esters in the presence of 3-aryl-2H-azirines having no substituent in the 2-position gives rise to azirinium ylides which then undergo isomerization into 2-azabuta-1,3-diene derivatives or (in the presence of excess diazo ester) react with the corresponding rhodium carbenoid to form substituted 3,4-dihydro-2H-pyrroles. 2-Mono-and 2,2-disubstituted 3-phenyl-2H-azirines react with rhodium carbenoids generated from diazo esters to give azirinium ylides which are converted into the corresponding 2-azabuta-1,3-dienes.

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. Padwa, A. and Hornbuckle, S.F., Chem. Rev., 1991, vol. 91, p. 263.

    Article  CAS  Google Scholar 

  2. Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Adv. Heterocycl. Chem., 1996, vol. 65, p. 93.

    Article  CAS  Google Scholar 

  3. Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Usp. Khim., 2005, vol. 74, p. 183.

    Google Scholar 

  4. Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Ros. Khim. Zh., 1999, vol. 43, p. 70.

    CAS  Google Scholar 

  5. Gilchrist, T.L., Aldrichim. Acta, 2001, vol. 34, p. 51.

    CAS  Google Scholar 

  6. Zwanenburg, B. and ten Holte, P., Top. Cur. Chem., 2001, vol. 216, p. 93.

    Article  CAS  Google Scholar 

  7. Palacios, F., Ochoa de Retana, A.M., Martynez de Marigorta, E., and de los Santos, J.M., Eur. J. Org. Chem., 2001, p. 2401.

  8. Rai, K.M.L. and Hassner, A., Advances in Strained and Interesting Organic Molecules, Halton, B., Ed., Stamford: JAI, 2000, vol. 8, p. 187.

    Google Scholar 

  9. Hassner, A., Currie, J.O., Steinfeld, A.S., and Atkinson, R.F., J. Am. Chem. Soc., 1973, vol. 95, p. 2982.

    Article  CAS  Google Scholar 

  10. Khlebnikov, A.F., Novikov, M.S., and Amer, A.A., Tetrahedron Lett., 2002, vol. 43, p. 8523.

    Article  CAS  Google Scholar 

  11. Khlebnikov, A.F., Novikov, M.S., and Amer, A.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 1049.

  12. Nair, V., J. Org. Chem., 1968, vol. 33, p. 2121.

    Article  CAS  Google Scholar 

  13. Nair, V., J. Org. Chem., 1968, vol. 33, p. 4316.

    Article  Google Scholar 

  14. Komatsu, M., Nishikaz, N., Ohshiro, Y., and Agawa, T., J. Org. Chem., 1976, vol. 41, p. 3642.

    Article  CAS  Google Scholar 

  15. Khlebnikov, A.F., Nikiforova, T.Yu., and Kostikov, R.R., Russ. J. Org. Chem., 1996, vol. 32, p. 715.

    Google Scholar 

  16. Tsuge, O., Ueno, K., Kanemasa, S., and Yorozu, K., Bull. Chem. Soc. Jpn., 1986, vol. 59, p. 1809.

    CAS  Google Scholar 

  17. Achiwa, K., Sugiyama, K., and Sekiya, M., Chem. Pharm. Bull., 1985, vol. 33, p. 1975.

    CAS  Google Scholar 

  18. Achiwa, K., Sugiyama, K., and Sekiya, M., Tetrahedron Lett., 1982, vol. 23, p. 2589.

    Article  CAS  Google Scholar 

  19. Joucla, M., Gree, D., and Hamelin, J., Tetrahedron, 1973, vol. 29, p. 2315.

    Article  CAS  Google Scholar 

  20. Schulthess, H. and Hansen, H.-J., Helv. Chim. Acta, 1981, vol. 64, p. 1322.

    Article  CAS  Google Scholar 

  21. Fowler, F.W., Hassner, A., and Levy, L.A., J. Am. Chem. Soc., 1967, vol. 89, p. 2077.

    Article  CAS  Google Scholar 

  22. Hortmann, G., Robertson, D.A., and Gillard, B.K., J. Org. Chem., 1972, vol. 37, p. 322.

    Article  CAS  Google Scholar 

  23. Khlebnikov, A.F., Novikov, M.S., and Amer, A.A., Tetrahedron Lett., 2004, vol. 45, p. 6003.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. F. Khlebnikov, M. S. Novikov, A. A. Amer & R. R. Kostikov

  2. Institut für anorganische Chemie, Georg-August-Universitat, Tammannstrasse 4, Göttingen, D37077, Germany

    J. Magull & D. Vidovic

Authors
  1. A. F. Khlebnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. S. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Amer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. R. Kostikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J. Magull
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. D. Vidovic
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © A.F. Khlebnikov, M.S. Novikov, A.A. Amer, R.R. Kostikov, J. Magull. D. Vidovic, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 4, pp. 533–544.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khlebnikov, A.F., Novikov, M.S., Amer, A.A. et al. Azirinium ylides from alkoxycarbonylcarbenoids and 2H-azirines: Generation and transformations. Russ J Org Chem 42, 515–526 (2006). https://doi.org/10.1134/S1070428006040075

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428006040075

Keywords

Search

Navigation