Skip to main content
Log in

Synthesis and complexing properties of a double-calix[4]arene crown ether

  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

Treatment ofp-tert-butylcalix[4]arene with tetraethyleneglycol ditosylate in the presence of potassium carbonate in acetonitrile afforded the first example of a double-calixcrown (1) in 52% yield. The double-calixcrown (1) was shown to form 1: 1 complexes with potassium and rubidium picrates in the solid state and in solution in chloroform. The stability constants of the alkali complexes have been determined in acetonitrile, as well as the phase transfer parameters from water to dichloromethane.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. J.-M. Lehn:Chem. Scr. 28, 237 (1988). (b) D. J. Cram:Chem. Scr. 28, 263 (1988).

    Google Scholar 

  2. C. D. Gutsche: inCalixarenes: A Versatile Class of Macrocyclic Compounds, J. Vicens and V. Böhmer (Eds), Kluwer Academic Publishers, Dordrecht, Holland, 1991.

    Google Scholar 

  3. E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A. A. El-Fald, and D. J. Reinhoudt:J. Am. Chem. Soc. 112, 6979 (1990) and references therein.

    Google Scholar 

  4. P. J. Dijkstra, J. A. Brunik, K. E. Bugge, D. J. Reinhoudt, S. Harkema, R. Ungaro, F. Ugozzoli, and E. Ghidini:J. Am. Chem. Soc. 111, 7567 (1989) and references therein.

    Google Scholar 

  5. C. D. Gutsche and M. Iqbal:Org. Synth. 68, 234 (1989).

    Google Scholar 

  6. F. Arnaud-Neu, S. Cremin, D. Cunningham, S. J. Harris, P. McCardle, M. A. McKervey, M. McManus, M. J. Schwing-Weill, K. Ziat:J. Incl. Phenom. 10, 329 (1991).

    Google Scholar 

  7. F. Arnaud-Neu, E. M. Collins, M. Deasy, G. Ferguson, S. J. Harris, B. Kaitner, A. J. Lough, M. A. McKervey, E. M. Margues, B. L. Ruhl, M. J. Schwing-Weill, E. M. Seward:J. Am. Chem. Soc. 111, 8681 (1989).

    Google Scholar 

  8. J. D. van Loon, D. Kraft, M. J. K. Ankoné, W. Verboom, S. Harkema, W. Vogt, V. Böhmer, and D. J. Reinhoudt:J. Org. Chem. 55, 5176 (1990).

    Google Scholar 

  9. C. Alfieri, E. Dradi, A. Pochini, R. Ungaro, and G. D. Andretti:J. Chem. Soc. Chem. Commun. 1075 (1983).

  10. K. Iwamoto, K. Fujimoto, T. Matsada, and S. Shinkai:Tetrahedron Lett. 7169, (1990) and references therein.

  11. R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen, and D. Sen:Chem. Rev. 85, 271 (1985).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Asfari, Z., Abidi, R., Arnaud, F. et al. Synthesis and complexing properties of a double-calix[4]arene crown ether. J Incl Phenom Macrocycl Chem 13, 163–169 (1992). https://doi.org/10.1007/BF01053640

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01053640

Key words

Navigation