Serendipitous one-pot formation of an unusual calix[5]arene-bis-crown-3 receptor

Tetrahedron Letters

Volumn 49, Issue 50, 2008, Pages 7146-7148

  Gattuso, Giuseppe ^a   Liotta, Claudia ^a   Notti, Anna ^a   Pappalardo, Sebastiano ^b   Parisi, Melchiorre F ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL; CALIX[5]ARENE BIS CROWN 3 RECEPTOR; CALIXARENE; CESIUM; CROWN ETHER DERIVATIVE; LITHIUM; POTASSIUM ION; RECEPTOR; RUBIDIUM; SODIUM ION; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTROSPRAY MASS SPECTROMETRY; GEOMETRY; METAL BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 54449097113     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.158     Document Type: Article

References (42)

1. Gutsche C.D. Calixarenes Revisited. In: Stoddart J.F. (Ed). Monographs in Supramolecular Chemistry Vol. 6 (1998), The Royal Society of Chemistry, Cambridge
2. Ikeda A., and Shinkai S. Chem. Rev. 97 (1997) 1713-1734
3. Böhmer V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713-745
4. Parisi M.F., and Pappalardo S. In: Katritzky A.R., Ramsden C.A., Scriven E.F.V., and Taylor R.J.K. (Eds). Comprehensive Heterocyclic Chemistry III Vol. 14 (2008), Elsevier, Oxford 667-750
5. Casnati A., Ungaro R., Asfari Z., and Vicens J. In: Asfari Z., Böhmer V., Harrowfield J., and Vicens J. (Eds). Calixarenes 2001 (2001), Kluwer Academic, Dordrecht 365-384
6. De Salvo G., Gattuso G., Notti A., Parisi M.F., and Pappalardo S. J. Org. Chem 67 (2002) 684-692
7. Gattuso M., Notti A., Pappalardo S., and Parisi M.F. Tetrahedron Lett 39 (1998) 1969-1972
8. Sgarlata V., Organo V.G., and Rudkevich D.M. Chem. Commun. (2005) 5630-5632
9. Organo V.G., Leontiev A.V., Sgarlata V., Dias H.V.R., and Rudkevich D.M. Angew. Chem., Int. Ed. 44 (2005) 3043-3047
10. Rudkevich D.M., Kang Y., Leontiev A.V., Organo V.G., and Zyryanov G.V. Supramol. Chem. 17 (2005) 93-99
11. Zyryanov G.V., and Rudkevich D.M. J. Am. Chem. Soc. 126 (2004) 4264-4270
12. Sidorov V., Kotch F.W., Davis J.T., and El-Kouedi M. Chem. Commun. (2000) 2369-2370
13. Atsushi I., and Shinkai S. J. Chem. Soc., Chem. Commun. (1994) 2375-2376
14. Izzo I., Licen S., Maulucci N., Autore G., Marzocco S., Tecilla P., and De Riccardis F. Chem. Commun. 26 (2008) 2986-2988
15. Maulucci N., De Riccardis F., Botta C.B., Casapullo A., Cressina E., Fregonese M., Tecilla P., and Izzo I. Chem. Commun. 10 (2005) 1354-1356
16. Leevy W.M., Huettner J.E., Pajewski R., Schlesinger P.H., and Gokel G.W. J. Am. Chem. Soc. 126 (2004) 15747-15753
17. Djedovic N., Ferdan R., Harder E., Pajewska J., Pajewski R., Schlesinger P.H., and Gokel G.W. Chem. Commun. 23 (2003) 2862-2863
18. Schmitt P., Beer P.D., Drew M.G.B., and Sheen P.D. Angew. Chem., Int. Ed. 36 (1997) 1840-1842
19. Matthews S.E., Schmitt P., Felix V., Drew M.G.B., and Beer P.D. J. Am. Chem. Soc. 124 (2002) 1341-1353
20. Notti A., Occhipinti S., Pappalardo S., Parisi M.F., Pisagatti I., White A.J.P., and Williams D.J. J. Org. Chem. 67 (2002) 7569-7572
21. Stewart D.R., and Gutsche D.C. Org. Prep. Proced. Int. 25 (1993) 137-139
22. Makha M., Nichols P.J., Hardie M.J., and Raston C.L. J. Chem. Soc., Perkin Trans. 1 (2002) 354-359
23. Benco J.S., Nienaber H.A., Dennen K., and McGimpsey W.G. J. Photochem. Photobiol. A: Chem. 152 (2002) 33-40
24. Markowitz M.A., Janout V., Castner D.G., and Regen S.L. J. Am. Chem. Soc. 111 (1989) 8192-8200
25. Haino T., Yanase M., and Fukazawa Y. Tetrahedron Lett. 38 (1997) 3739-3742
26. Haino T., Yanase M., and Fukazawa Y. Angew. Chem., Int. Ed. Engl. 36 (1997) 259-260
27. 8: C, 76.07; H, 8.48. Found: C, 75.68; H, 8.52.
28. 15
29. Ferguson G., Notti A., Pappalardo S., Parisi M.F., and Spek A.L. Tetrahedron Lett. 39 (1998) 1965-1968
30. Bell S.E.J., Browne J.K., McKee V., McKervey M.A., Malone J.F., O'Leary M., and Walker A. J. Org. Chem. 63 (1998) 489-501
31. Jaime C., De Mendoza J., Prados P., Nieto P.M., and Sanchez C. J. Org. Chem. 56 (1991) 3372-3376
32. Pappalardo S. New J. Chem. 20 (1996) 465-472
33. Notti A., Parisi M.F., and Pappalardo S. In: Asfari Z., Böhmer V., Harrowfield J., and Vicens J. (Eds). Calixarenes 2001 (2001), Kluwer Academic, Dordrecht 54-70
34. Kraft D., Arnecke R., Böhmer V., and Vogt W. Tetrahedron 49 (1993) 6019-6024
35. 7: C, 76.60; H, 8.47. Found: C, 76.42; H, 8.49.
36. Calculations were performed with Spartan 06 (Wavefunction, Inc.).
37. Hehre W.J., Radom L., Schleyer P.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1985), Wiley, New York
38. For a discussion of calix[5]arene conformations, see:. Thondorf I., and Brenn J. J. Chem. Soc. Perkin Trans (1997) 2293-2299
39. Stewart D.R., Krawiec M., Kashyap R.P., Watson W.H., and Gutsche C.D. J. Am. Chem. Soc. 117 (1995) 586-601
40. Sherman C.L., and Brodbelt J.S. Anal. Chem. 37 (2003) 1828-1836
41. Ferguson G., Lough A.J., Notti A., Pappalardo S., Parisi M.F., and Resnati G. Collect. Czech. Chem. Commun. 69 (2004) 1109-1125
42. Gattuso G., Notti A., Pappalardo A., Parisi M.F., Pisagatti I., Pappalardo S., Garozzo D., Messina A., Cohen Y., and Slovak S. J. Org. Chem. 73 (2008) 7280-7289