Advertisement

Russian Journal of Organic Chemistry

, Volume 42, Issue 4, pp 515–526 | Cite as

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

  • A. F. Khlebnikov
  • M. S. Novikov
  • A. A. Amer
  • R. R. Kostikov
  • J. Magull
  • D. Vidovic
Article

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.

Keywords

Ester Organic Chemistry Diene Rhodium Dirhodium 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Padwa, A. and Hornbuckle, S.F., Chem. Rev., 1991, vol. 91, p. 263.CrossRefGoogle Scholar
  2. 2.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Adv. Heterocycl. Chem., 1996, vol. 65, p. 93.CrossRefGoogle Scholar
  3. 3.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Usp. Khim., 2005, vol. 74, p. 183.Google Scholar
  4. 4.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Ros. Khim. Zh., 1999, vol. 43, p. 70.Google Scholar
  5. 5.
    Gilchrist, T.L., Aldrichim. Acta, 2001, vol. 34, p. 51.Google Scholar
  6. 6.
    Zwanenburg, B. and ten Holte, P., Top. Cur. Chem., 2001, vol. 216, p. 93.CrossRefGoogle Scholar
  7. 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.Google Scholar
  8. 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. 9.
    Hassner, A., Currie, J.O., Steinfeld, A.S., and Atkinson, R.F., J. Am. Chem. Soc., 1973, vol. 95, p. 2982.CrossRefGoogle Scholar
  10. 10.
    Khlebnikov, A.F., Novikov, M.S., and Amer, A.A., Tetrahedron Lett., 2002, vol. 43, p. 8523.CrossRefGoogle Scholar
  11. 11.
    Khlebnikov, A.F., Novikov, M.S., and Amer, A.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 1049.Google Scholar
  12. 12.
    Nair, V., J. Org. Chem., 1968, vol. 33, p. 2121.CrossRefGoogle Scholar
  13. 13.
    Nair, V., J. Org. Chem., 1968, vol. 33, p. 4316.CrossRefGoogle Scholar
  14. 14.
    Komatsu, M., Nishikaz, N., Ohshiro, Y., and Agawa, T., J. Org. Chem., 1976, vol. 41, p. 3642.CrossRefGoogle Scholar
  15. 15.
    Khlebnikov, A.F., Nikiforova, T.Yu., and Kostikov, R.R., Russ. J. Org. Chem., 1996, vol. 32, p. 715.Google Scholar
  16. 16.
    Tsuge, O., Ueno, K., Kanemasa, S., and Yorozu, K., Bull. Chem. Soc. Jpn., 1986, vol. 59, p. 1809.Google Scholar
  17. 17.
    Achiwa, K., Sugiyama, K., and Sekiya, M., Chem. Pharm. Bull., 1985, vol. 33, p. 1975.Google Scholar
  18. 18.
    Achiwa, K., Sugiyama, K., and Sekiya, M., Tetrahedron Lett., 1982, vol. 23, p. 2589.CrossRefGoogle Scholar
  19. 19.
    Joucla, M., Gree, D., and Hamelin, J., Tetrahedron, 1973, vol. 29, p. 2315.CrossRefGoogle Scholar
  20. 20.
    Schulthess, H. and Hansen, H.-J., Helv. Chim. Acta, 1981, vol. 64, p. 1322.CrossRefGoogle Scholar
  21. 21.
    Fowler, F.W., Hassner, A., and Levy, L.A., J. Am. Chem. Soc., 1967, vol. 89, p. 2077.CrossRefGoogle Scholar
  22. 22.
    Hortmann, G., Robertson, D.A., and Gillard, B.K., J. Org. Chem., 1972, vol. 37, p. 322.CrossRefGoogle Scholar
  23. 23.
    Khlebnikov, A.F., Novikov, M.S., and Amer, A.A., Tetrahedron Lett., 2004, vol. 45, p. 6003.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • A. F. Khlebnikov
    • 1
  • M. S. Novikov
    • 1
  • A. A. Amer
    • 1
  • R. R. Kostikov
    • 1
  • J. Magull
    • 2
  • D. Vidovic
    • 2
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut für anorganische ChemieGeorg-August-UniversitatGöttingenGermany

Personalised recommendations