Calix[5]- And calix[8]arenes bridged with heterocycles

European Journal of Organic Chemistry

Volumn , Issue 11, 2005, Pages 2330-2337

  Konrad, Serge ^a   Näther, Christian ^a   Lüning, Ulrich ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Bridges; Calixarenes; Heterocycles; Macrocycles; Supramolecular chemistry

Indexed keywords

EID: 20444500047     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400774     Document Type: Article

References (35)

1. C. D. Gutsche, M. Iqbal, Org. Synth. 1990, 68, 234-237.
2. C. D. Gutsche, B. Dhawan, M. Leonis, D. Stewart, Org. Synth. 1990, 68, 238-242.
3. J. H. Munch, C. D. Gutsche, Org. Synth. 1990, 68, 243-246.
4. C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, 1989 and 1992.
5. C. D. Gutsche, Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, 1998.
6. Z. Asfari, V. Böhmer, J. M. Harrowfield, J. Vicens (Eds.), Calixarenes 2001, Kluwer Academic Publishers, Dordrecht, 2001.
7. L. Mandolini (Ed.), Calixarenes in Action, Imperial College Press, London, 2000.
8. J. Vicens, V. Böhmer, Calixarenes, A Versatile Class of Macrocyclic Compounds, Kluwer Academic Press, Dordrecht, 1991.
9. Y. Chen, S. Gong, J. Incl. Phenom. Macrocycl. Chem. 2003, 45, 165-184.
10. H. ROSS, U. Lüning, Angew. Chem. 1995, 107, 2723-2725;
11. Angew. Chem. Int. Ed. Engl. 1995, 34, 2555-2557.
12. H. Ross, U. Lüning, Tetrahedron Lett. 1997, 38, 4539-4542.
13. U. Lüning, H. Ross, I. Thondorf, J. Chem. Soc., Perkin Trans. 2 1998, 1313-1317, and references cited therein.
14. P. Neri, G. M. L. Consoli, F. Cunsolo, C. Geraci, M. Piattelli in Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. M. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, 2001.
15. J. L. Atwood, J. Steed (Eds.) Encyclopedia of Supramolecular Chemistry, Marcel Dekker, New York, 2004.
16. U. Lüning, M. Hagen, F. Löffler, T. Marquardt, B. Meynhardt, J. Incl. Phen. Mol. Recogn. Chem. 1999, 55, 381-387.
17. F. Löffler, M. Hagen, U. Lüning, Synlett 1999, 1826-1828, and references cited therein.
18. M. Bühl, F. Terstegen, F. Löffler, B. Meynhardt, S. Kierse, M. Müller, C. Näther, U. Lüning, Eur. J. Org. Chem. 2001, 2151-2160.
19. D. R. Stewart, C. D. Gutsche, Org. Prep. Proced. Int. 1993, 25, 137-139.
20. D. Kraft, R. Arnecke, V. Böhmer, W. Vogt, Tetrahedron 1993, 49, 6019-6024.
21. S. Pappalardo, M. F. Parisi, J. Org. Chem. 1996, 61, 8724-8725.
22. A. Notti, M. F. Parisi, S. Pappalardo in Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. M. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, 2001.
23. J. P. W. Eggert, J. Harrowfield, U. Lüning, B. W. Skelton, A. H. White, F. Löffler, S. Konrad, Eur. J. Org. Chem. 2005, 1348-1353.
24. D. Garozzo, G. Gattuso, F. H. Kohnke, A. Notti, S. Pappalardo, M. F. Parisi, I. Pisagatti, A. J. P. White, D. J. Williams, Org. Lett. 2003, 5, 4025-4028.
25. With an acridone-containing bridge, a mixture of products was obtained from which a [1+1] bridged calix[8]arene and a [2+1] bis-calix[8]arene were isolated in low yields by preparative TLC: Y. S. Tsantrizos, W. Chew, L. D. Colebrook, F. Sauriol, Tetrahedron Lett. 1997, 38, 5411-5414.
26. C. Gaeta, L. Gregoli, M. Martine, P. Neri, Tetrahedron Lett. 2002, 43, 8875-8878.
27. A. Ikeda, K. Akao, T. Harada, S. Shinkai, Tetrahedron Lett. 1996, 37, 1621-1624.
28. U. Lüning, M. Müller, Liebigs Ann. Chem. 1989, 367-374.
29. U. Lüning, R. Baumstark, M. Müller, Liebigs Ann. Chem. 1991, 987-998.
30. E. Weber, F. Vögtle, H.-P. Josel, G. R. Newkome, W. E. Pucket, Chem. Ber. 1983, 116, 1906-1913.
31. M. A. Masood, D. J. Hodgson, Inorg. Chem. 1993, 32, 4839-4844.
32. H. Takalo, P. Pasanen, J. Kankare, Acta Chem. Scand., Ser. B. 1988, 42, 373.
33. C. D. Gutsche, L.-G. Lin, Tetrahedron 1986, 42, 1633-1640.
34. 2-Ar signals could not be separated, even by DEPT.
35. 13C NMR spectrum even at 75°C (caused by a high coalescence temperature) the spectrum cannot be interpreted fully.