Russian Journal of Organic Chemistry

, Volume 38, Issue 5, pp 672–682 | Cite as

1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from Schiff Bases and Difluorocarbene to Symmetric Olefins

  • M. S. Novikov
  • A. F. Khlebnikov
  • E. S. Sidorina
  • A. E. Masalev
  • J. Kopf
  • R. R. Kostikov
Article

Abstract

Difluoro(iminio)methanides generated by the action of difluorocarbene on Schiff bases react with derivatives of maleic and fumaric acids, following the 1,3-dipolar cycloaddition pattern to give 2,2-difluoropyrrolidines which were detected by gas chromatography-mass spectrometry. The final products are stereo-isomeric substituted 2-pyrrolidinones formed by hydrolysis of difluoropyrrolidines and their dehydrofluorination products, 2-fluoro-4,5-dihydropyrroles. The observed stereoselectivity of the cycloaddition suggests Z configuration of intermediate ylide and both endo- and exo-approach to the dipolarophile in the transition state corresponding to cycloaddition.

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REFERENCES

  1. 1.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Adv. Heterocycl. Chem., Katritzky, A.R., Ed., San Diego: Academic, 1996, vol. 65, pp. 93-233.Google Scholar
  2. 2.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Khim. Geterotsikl. Soedin., 1987, no. 10, pp. 1336-1342.Google Scholar
  3. 3.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Zh. Org. Khim., 1988, vol. 24, no. 9, pp. 1917-1922.Google Scholar
  4. 4.
    Novikov, M.S., Khlebnikov, A.F., and Kostikov, R.R., Russ. J. Org. Chem., 1996, vol. 32, no. 5, pp. 637-644.Google Scholar
  5. 5.
    Khlebnikov, A.F., Nikiforova, T.Yu., and Kostikov, R.R., Russ. J. Org. Chem., 1996, vol. 32, no. 5, pp. 715-728.Google Scholar
  6. 6.
    Khlebnikov, A.F., Novikov, M.S., Nikiforova, T.Yu., and Kostikov, R.R., Russ. J. Org. Chem., 1999, vol. 35, no. 1, pp. 91-99.Google Scholar
  7. 7.
    Khlebnikov, A.F. and Kostikov, R.R., Khim. Getero-tsikl. Soedin., 1987, no. 6, p. 856.Google Scholar
  8. 8.
    Khlebnikov, A.F., Kostik, E.I., Kostikov, R.R., and Bespalov, V.Ya., Khim. Geterotsikl. Soedin., 1990, no. 3, pp. 355-362.Google Scholar
  9. 9.
    Khlebnikov, A.F., Kostik, E.I., and Kostikov, R.R., Synthesis, 1993, no. 6, pp. 568-570.Google Scholar
  10. 10.
    Khlebnikov, A.F., Kostik, E.I., Kopf, J., Aleksandrov, E.V., and Kostikov, R.R., Russ. J. Org. Chem., 1998, vol. 34, no. 5, pp. 712-724.Google Scholar
  11. 11.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Zh. Org. Khim., 1990, vol. 26, no. 9, pp. 1899-1903.Google Scholar
  12. 12.
    Khlebnikov, A.F., Kostik, E.I., and Kostikov, R.R., Russ. J. Org. Chem., 1998, vol. 34, no. 4, pp. 541-542.Google Scholar
  13. 13.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Ross. Khim. Zh., 1999, vol. 43, no. 1, pp. 70-79.Google Scholar
  14. 14.
    Novikov, M.S., Khlebnikov, A.F., Masalev, A.E., and Kostikov, R.R., Tetrahedron Lett., 1997, vol. 38, no. 23, pp. 4187-4190.Google Scholar
  15. 15.
    Fritz, H.P. and Kornrumpf, W.Z., Z. Naturforsch., Teil B: Anorg. Chem. Org. Chem., 1981, vol. 36, no. 11, pp. 1375-1380.Google Scholar
  16. 16.
    Khlebnikov, A.F., Novikov, M.S., and Kostikov, R.R., Mendeleev Commun., 1997, pp. 145-147.Google Scholar
  17. 17.
    Novikov, M.S., Khlebnikov, A.F., Sidorina, E.S., and Kostikov, R.R., J. Chem. Soc., Perkin Trans. 1, 2000, no. 2, pp. 231-237.Google Scholar
  18. 18.
    Tsuge, O., Ueno, K., Kanemasa, S., and Yorozu, K., Bull. Chem. Soc. Jpn., 1986, vol. 59, no. 6, pp. 1809-1824.Google Scholar
  19. 19.
    Achiwa, K., Sugiyama, K., and Sekiya, M., Chem. Pharm. Bull., 1985, vol. 33, no. 5, pp. 1975-1981.Google Scholar
  20. 20.
    Achiwa, K. and Sekiya, M., Tetrahedron Lett., 1982, vol. 23, no. 25, pp. 2589-2592.Google Scholar
  21. 21.
    Jouela, M., Gree, D., and Hamelin, J., Tetrahedron, 1973, vol. 29, no. 15, pp. 2315-2322.Google Scholar
  22. 22.
    Tsuge, O., Kanemasa, S., and Takenaka, S., Bull. Chem. Soc. Jpn., 1985, vol. 58, no. 11, pp. 3137-3157.Google Scholar
  23. 23.
    Amornraksa, K., Grigg, R., Gunaratne, H.Q.N., Kemp, J., and Sridharan, V., J. Chem. Soc., Perkin Trans. 1, 1987, pp. 2285-2296.Google Scholar
  24. 24.
    Padwa, A. and Ku, H., J. Org. Chem., 1979, vol. 44, no. 2, pp. 255-261.Google Scholar
  25. 25.
    Mashchenko, N.V., Matveeva, A.T., Odinets, I.L., Matrosov, E.I., Petrov, E.S., Terekhova, M.I., Matveev, A.K., Mastryukova, T.A., and Kabach-nik, M.I., Zh. Obshch. Khim., 1988, vol. 58, no. 9, pp. 1973-1979.Google Scholar
  26. 26.
    Tsuge, O., Kanemasa, S., and Matsuda, K., J. Org. Chem., 1984, vol. 49, no. 15, pp. 2688-2691.Google Scholar
  27. 27.
    Organic Syntheses, Horning, E.C., Ed., New York: Wiley, 1947, coll. vol. 3. Translated under the title Sintezy organicheskikh preparatov, Moscow: Inost-rannaya Literatura, 1956, vol. 6, p. 150.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2002

Authors and Affiliations

  • M. S. Novikov
    • 1
  • A. F. Khlebnikov
    • 1
  • E. S. Sidorina
    • 1
  • A. E. Masalev
    • 1
  • J. Kopf
    • 2
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut für Anorganische ChemieHamburgGermany

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