Skip to main content
SpringerLink
Log in

Selective Upper-Rim Adamantylation of Calix[4]arenes

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

Abstract

Lower-rim mono- and diacylated calix[4]arenes [acyl = C6H5CO, 3,5-(NO2)2C6H3CO] undergo selective adamantylation with 3-Y-1-adamantanols (Y = H, i-Pr, 4-MeC6H4) in trifluoroacetic acid at the free phenolic fragments of the macroring. The reaction provides a convenient preparative route to di-, tri-, and tetraadamantylated calix[4]arenes.

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. Gutsche, C.D., Host Guest Complex Chemistry: Macrocycles: Synthesis, Structures, Applications, Vögtle, F. and Weber, E., Eds., Berlin: Springer, 1985. Translated under the title Khimiya kompleksov “gost'–khozyain.” Sintez, struktury i primenenie, Moscow: Mir, 1988, pp. 445-495.

    Google Scholar 

  2. Gutsche, C.D., Calixarenes: Monographs in Supramolecular Chemistry, Stoddart, J.F., Ed., Cambridge: The Royal Society of Chemistry, 1989, vol. 1, p. 1.

    Google Scholar 

  3. Bohmer, V., Angew. Chem., 1995, vol. 107, no. 4, pp. 785-818.

    Google Scholar 

  4. Lubitov, I., Shokova, E., and Kovalev, V., Synlett., 1993, no. 9, pp. 647-649.

  5. Khomich, A.N., Shokova, E.A., and Kovalev, V.V., Synlett., 1994, no. 12, pp. 1027-1028.

  6. Kovalev, V., Shokova, E., and Khomich, E., Abstracts of Papers, 4th Int. Conf. on Calixarenes, Parma, Italy, August 31–September 4, 1997, p. 140.

    Google Scholar 

  7. Kovalev, V., Shokova, E., Khomich, A., and Luzikov, Yu., New J. Chem., 1996, vol. 20, no. 4, pp. 483-492.

    Google Scholar 

  8. Shokova, E., Khomich, A., and Kovalev, V., Tetrahedron Lett., 1996, vol. 37, no. 4, pp. 543-546.

    Google Scholar 

  9. See, K.A., Fronczek, F.R., Watson, W.H., Kashyap, R.P., and Gutsche, C.D., J. Org. Chem., 1991, vol. 56, no. 26, pp. 7256-7268.

    Google Scholar 

  10. Gutsche, C., Iqbal, M., and Stewart, D., J. Org. Chem., 1986, vol. 51, no. 5, pp. 742-745.

    Google Scholar 

  11. Gutsche, C. and Lin, L., Tetrahedron, 1986, vol. 42, no. 6, pp. 1633-1640.

    Google Scholar 

  12. Arduini, A., Fabbi, M., Mantovani, M., Mirone, L., Pochini, A., Secchi, A., and Ungaro, R., J. Org. Chem., 1995, vol. 60, no. 5, pp. 1454-1457.

    Google Scholar 

  13. Linnane, P., James, T.D., and Shinkai, S., J. Chem. Soc., Chem. Commun., 1995, no. 19, pp. 1997-1998.

  14. Van Loon, J.-D., Arduini, A., Verboom, W., Ungaro, R., van Hummel, G., Harkema, S., and Reinhoudt, D., Tetrahedron Lett., 1989, vol. 30, no. 20, pp. 2681-2684.

    Google Scholar 

  15. Chun-mei Shu, Wen-chin Liu, Ming-chung Ku, Fa-shin Tang, Mei-ling Yeh, and Lee-gin Lin, J. Org. Chem., 1994, vol. 59, no. 13, pp. 3730-3733.

    Google Scholar 

  16. Kanamathareddy, S. and Gutsche, C., J. Org. Chem., 1995, vol. 60, no. 19, pp. 6070-6075.

    Google Scholar 

  17. Stetter, H., Schwarz, M., and Hirschhorn, A., Chem. Ber., 1959, vol. 92, no. 7, pp. 1629-1635.

    Google Scholar 

  18. Shokova, E.A., Knopova, S.I., Nguen Dang K'en, and Kazanskii, B.A., Neftekhimiya, 1973, vol. 13, no. 4, pp. 585-591.

    Google Scholar 

  19. Kovalev, V., Rozov, A., and Shokova, E., Tetrahedron, 1996, vol. 52, no. 11, pp. 3983-3990.

    Google Scholar 

  20. Kovalev, V.V., Knyazeva, I.V., and Shokova, E.A., Zh. Org. Khim., 1986, vol. 22, no. 4, pp. 776-780.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, 119899, Russia

    E. A. Shokova, A. N. Khomich & V. V. Kovalev

Authors
  1. E. A. Shokova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. N. Khomich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Kovalev
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shokova, E.A., Khomich, A.N. & Kovalev, V.V. Selective Upper-Rim Adamantylation of Calix[4]arenes. Russian Journal of Organic Chemistry 37, 612–619 (2001). https://doi.org/10.1023/A:1012423128245

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012423128245

Keywords

Search

Navigation