Calix crowns derived from para-bridged calix[4]arenes

Organic Letters

Volumn 2, Issue 6, 2000, Pages 839-841

  Stephan, H ^a   Gloe, K ^a   Paulus, E F ^b   Saadioui, M ^b   Bohmer V ^c  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b SANOFI   (France)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000262845     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005581b     Document Type: Article

References (23)

1. For recent reviews on calixarenes see for example: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745;
2. (b) Gutsche, C. D. Calixarenes Revisited; RSC Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, U.K., 1998.
3. For reviews on calixarene-derived ionophores see: McKervey, M. A.; Schwing-Weill, M.-J.: Arnaud-Neu, F. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon: Oxford, U.K., 1996; Vol. 1, p 537.
4. Schwing-Weill, M.-J.; Arnaud-Neu, F.; McKervey, M. A. J. Phys. Org. Chem. 1992, 5, 496-501.
5. Casnati, A.; Pochini, A.; Ungaro, R.; Bocchi, C.; Ugozzoli, F.; Egberink, R. J. M.; Struijk, H.; Lugtenberg, R.; de Jong, F.; Reinhoudt, D. N. Chem. Eur. J. 1996, 2, 436-445.
6. Ungaro, R.; Casnati, A.; Ugozzoli, F.; Pochini, A.; Dozol, J.-F.; Hill, C.; Rouquette, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1506-1509.
7. Dozol, J.-F.; Simon, N.; Lamare, V.; Rouquette, H.; Eymard, S.; Tournois, B.; De Marc, D.; Macias, R. M. Sep. Sci. Technol. 1999, 34, 877-909.
8. (a) Hill, C.; Dozol, J.-F.; Lamare, V.; Rouquette, H.; Eymard, S.; Tournois, B.; Vicens, J.; Asfari, Z.; Bressot, C.; Ungaro, R.; Casnati, A. J. Incl. Phenom. 1994, 19, 399-408;
9. (b) Sachleben, R. A.; Urvoas, A.; Bryan, J. C.; Haverlock, T. J.; Hay, B. P.; Moyer, B. A. Chem. Commun. 1999, 1751-1752.
10. Arnaud-Neu, F.; Böhmer, V.; Guerra, L.; McKervey, M. A.; Paulus, E. F.; Rodriguez, A.; Schwing-Weill, M.-J.; Tabatabai. M.; Vogt, W. J. Phys. Org. Chem. 1992, 5, 471-481.
11. Goldmann, H.; Vogt, W.; Paulus, E.; Böhmer, V. J. Am. Chem. Soc. 1988, 110, 6811-6817.
12. Reinhoudt, D. N.; de Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 20, 2067-2070. Compare also: Ghidini, E.; Ugozzoli, F.; Ungaro, R.; Harkema, S.; Abu El-Fadl, A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1990, 112, 6979-6985.
13. Reinhoudt, D. N.; de Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 20, 2067-2070. Compare also: Ghidini, E.; Ugozzoli, F.; Ungaro, R.; Harkema, S.; Abu El-Fadl, A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1990, 112, 6979-6985.
14. General procedure for the synthesis of crown ethers 5a - d: a solution of the bridged calixarene 4 (0.5 mmol) in 30 mL of dry acetonitrile was refluxed with 2 mmol of CsF for 1 h to give a clear solution. Then 0.5 mmol of the corresponding glycol ditosylate, dissolved in 20 mL of acetonitrile, was added slowly over a period of 4 h and reflux was continued for 24 h (or longer if TLC control showed still the presence of unreacted
15. 8 848.52).
16. See for instance: (a) Berger, B.; Böhmen, V.; Paulus,E.; Vogt, W. Angew. Chem., Int. Ed. Engl. 1992, 31, 96-99.
17. (b) Wasikiewicz, W.; Rokicki, G.; Kielkiewicz, J.; Paulus, E. F.; Böhmer, V. Monatsh. Chem. 1997, 128, 863-879.
18. 3, P1, 6629 reflections (-12 ≤ h ≤ 0, - 15 ≤ k ≤ 14, -16 ≤ l ≤
19. 3. The mean standard deviations are as follows: C-C bond, 0.005 Å; C-O bond, 0.005 Å; C-C-C bond angles, 0.4°, C-C-C-C torsion angles, 0.5°. All calculations were done by a DEC 3000/900 AXP and a Pentium PC computer with the SHELXTL-PLUS programs (Sheldrick, G. M. University of Göttingen, Göttingen, Germany, 1993 -1997).
20. Böhmer, V.; Goldmann, H.; Vogt, W.; Paulus, E. F.; Tobiason, F. L.; Thielman, M. J. J. Chem. Soc.. Perkin Trans. 2 1990, 1769-1775.
21. 45Ca in a liquid scintillation counter (Tricarb 2500, Canberra-Packard). For further details see ref 17.
22. + are extracted into the organic phase (%E < 0.5%).
23. Schmitz, J.; Vögtle, F.; Nieger, M.; Gloe, K.; Stephan, H.; Heitzsch, O.; Buschmann, H.-J. Supramol. Chem. 1994, 4, 115-119.