Advertisement

Russian Journal of Organic Chemistry

, Volume 45, Issue 8, pp 1168–1174 | Cite as

Catalytic [2+1]-cycloaddition of ethyl diazoacetate to fullerene [60]

  • A. R. Tuktarov
  • A. R. Akhmetov
  • R. F. Kamalov
  • L. M. Khalilov
  • M. Pudas
  • A. G. Ibragimov
  • U. M. Dzhemilev
Article

Abstract

Cyclopropanation of C60-fullerene was performed with ethyl diazoacetate in the presence of Pd(PPh3)4 catalyst. A probable reaction mechanism is suggested.

Keywords

Fullerene Methine Proton Thermal Isomerization Ethyl Diazoacetate Probable Reaction Mechanism 
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.
    De la Torre, M.D.L., Tome, A.C., Silva, A.M.S., and Cavalerio, J.A.S., Tetrahedron Lett., 2002, vol. 43, p. 4617.CrossRefGoogle Scholar
  2. 2.
    Pellicciari, R., Annibali, D., Costantino, G., Marinozzi, M., and Natalini, B., Synlett., 1997, p. 1196.Google Scholar
  3. 3.
    Warton, T., Kini, U.V., Mortis, R.A., and Wilson, L.J., Tetrahedron Lett., 2001, vol. 42, p. 5159.CrossRefGoogle Scholar
  4. 4.
    Nakamura, E., Tokuyama, H., Yamago, S., Shivaki, T., and Sugiura, Y., Bull. Chem. Soc. Jpn., 1996, vol. 69, p. 2143.CrossRefGoogle Scholar
  5. 5.
    Friedman, S.H., Ganapathi, P.S., Rubin, Y., and Kenyon, G.L., J. Med. Chem., 1998, vol. 41, p. 2424.CrossRefGoogle Scholar
  6. 6.
    Dugan, L.L., Turetsky, D.M., Du, C., Lobner, D., Wheeler, M., Almli, C.R., Shen, C.K.-F., Luh, T.-Y., Choi, D.W., and Lin, T.-S., Proc. Natl. Acad. Sci. USA, 1997, vol. 94, p. 9434.CrossRefGoogle Scholar
  7. 7.
    Huang Y.L., Shen, C.K., Luh, T.Y., Yang, H.C., Hwang, K.C., and Chou, C.K., Eur. J. Biochem., 1998, vol. 254, p. 38.CrossRefGoogle Scholar
  8. 8.
    Bingel, C., Chem. Ber., 1993, vol. 126, p. 1957.CrossRefGoogle Scholar
  9. 9.
    Suzuki, T., Li, Q., Khemani, K.C., Wudl, F., and Almarsson, O., Science, 1991, vol. 254, p. 1186.CrossRefGoogle Scholar
  10. 10.
    Smith, A.B. III, Strongin, R.M., Brard, L., Furst, G.T., Romanow, W.J., Owens, K.G., Goldschimdt, R.J., and King, R.C., J. Am. Chem. Soc., 1995, vol. 117, p. 5492.CrossRefGoogle Scholar
  11. 11.
    Isaacs, L., Wehtsig, A., and Diederich, F., Helv. Chim. Acta, 1993, vol. 76, p. 1231.CrossRefGoogle Scholar
  12. 12.
    Bestman, H.J. and Moll, C., Synlett., 1996, p. 729.Google Scholar
  13. 13.
    Suda, M., Synthesis, 1981, vol. 9, p. 714.CrossRefGoogle Scholar
  14. 14.
    Dzhemilev, U.M., Dokichev, V.A., Sultanov, S.Z., Khusnutdinov, R.I., Tomilov, Yu.V., Nefedov, O.M., and Tolstikov, G.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, p. 1861.Google Scholar
  15. 15.
    Blickle, P., Bloch, M., and Jones, T.B., Chem. Ber., 1979, vol. 112, p. 3691.CrossRefGoogle Scholar
  16. 16.
    Dent, W.T., Long, R., and Wilkinson, J., J. Chem. Soc., 1964, p. 1585.Google Scholar
  17. 17.
    Marvanov, R.M., Fakhretdinov, R.M., and Dzhemilev, U.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1985, p. 1680.Google Scholar
  18. 18.
    Tomilov, Yu.V., Kostitsyn, A.B., Dokichev, V.A., Dzhemilev, U.M., and Nefedov, O.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, p. 2752.Google Scholar
  19. 19.
    Dzhemilev, U.M., Dokichev, V.A., Maidanova, I.O., Nefedov, O.M., and Tomilov, Yu.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1993, p. 733.Google Scholar
  20. 20.
    Liu Y., Liu, P., Zhao, Z.-Y., Liu, S.-M., and Yin, Y.-Q., Applied Catalysis. A: General, 1998, 167L1.Google Scholar
  21. 21.
    Dzhemilev, U.M., Popod’ko, N.R., and Kozlova, E.V., Metallokompleksnyi kataliz v organicheskom sinteze (Metall Complex Catalysis in Organic Chemistry), Moscow: Khimiya, 1999, p. 110.Google Scholar
  22. 22.
    Bashilov, V.V., Tumanskii, B.L., and Petrovskii, P.V., Sokolov, V.I., Izv. Akad. Nauk, Ser. Khim., 1999, p. 575.Google Scholar
  23. 23.
    Magdesieva, T.V., Kravchuk, D.N., Bashilov, V.V., Kuznetsova, I.V., Sokolov, V.I., and Butin, K.P., Izv. Akad. Nauk, Ser. Khim., 2002, p. 1459.Google Scholar
  24. 24.
    Tomilov, Yu.V., Dokichev, V.A., Dzhemilev, U.M., and Nefedov, O.M., Usp. Khim., 1993, vol. 62, p. 847.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • A. R. Tuktarov
    • 1
  • A. R. Akhmetov
    • 1
  • R. F. Kamalov
    • 1
  • L. M. Khalilov
    • 1
  • M. Pudas
    • 2
  • A. G. Ibragimov
    • 1
  • U. M. Dzhemilev
    • 1
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussia
  2. 2.Microelectronics and Material Physics Laboratories, EMPART Research Group of Infotech Oulu, LinnanmaaUniversity of OuluOuluFinland

Personalised recommendations