Inclusion of organic cations by calix[4]arenes bearing cyclohepta-2,4,6-trienyl substituents

European Journal of Organic Chemistry

Volumn , Issue 8, 2001, Pages 1549-1561

  Orda Zgadzaj, Marzena ^a   Wendel, Volker ^a   Fehlinger, Matthias ^a   Ziemer, Burkhard ^a   Abraham, Werner ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Calixarenes; Cycloheptatriene; Host guest chemistry; Iminium ions; Tropylium ions

Indexed keywords

AMMONIA; CALIXARENE; CALIX[4]ARENE DERIVATIVE; CATION; CYCLOHEPTA 2,4,6 TRIENYL DERIVATIVE; PHENYL GROUP; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; SYNTHESIS;

EID: 0035049173     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200104)2001:8<1549::AID-EJOC1549>3.0.CO;2-X     Document Type: Article

References (47)

1. [1a] C. D. Gutsche, Calixarenes, Royal Society of Chemistry, Cambridge, England, 1989.
2. [1b] Calixarenes: A Versatile Class of Macrocyclic Compounds (Eds.: J. Vicens, V. Böhmer), Kluwer, Dordrecht, 1991, vol. 3.
3. [1c] A. Pochini, R. Ungaro in Comprehensive Supramolecular Chemistry, vol. 2 (Ed.: F. Vögtle), Pergamon, Oxford, 1996, pp. 103-142.
4. J.-C. G. Bünzli, J. M. Harrowfield in Calixarenes: A Versatile Class of Macrocyclic Compounds (Eds.: J. Vicens, V. Böhmer), Kluwer Academic Publishers, Dordrecht, 1991, p. 211.
5. G. E. Hofmeister, E. Alvarado, J. A. Leary, D. I. Yoon, S. F. Petersen, J. Am. Chem. Soc. 1989, 111, 2318-2319.
6. J. M. Harrowfield, M. I. Ogden, W. R. Richmond, B. W. Skelton, A. H. White, J. Chem. Soc., Perkin Trans. 2 1993, 2183-2190.
7. D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24.
8. J. M. Harrowfield, W. R. Richmond, A. N. Sobolev, J. Incl. Phen. Mol. Rec. 1994, 19, 257-276.
9. J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324.
10. A. Arduini, W. M. McGregor, D. Paganuzzi, A. Pochini, A. Secchi, F. Ugozzoli, R. Uncaro, J. Chem. Soc., Perkin Trans. 2 1996, 839-846.
11. K. Araki, H. Shimizu, S. Shinkai, Chem. Lett. 1993, 205-208.
12. F. Inokuchi, K. Araki, S. Shinkai, Chem. Lett. 1994, 1383-1386.
13. K. Araki, H. Hayashida, Tetrahedron Lett. 2000, 41, 1209-1213.
14. R. Arnecke, V. Böhmer, R. Cacciapaslia, A. D. Cort, L. Mandolini, Tetrahedron 1997, 53, 4901-4908.
15. B. Masci, M. Finelli, M. Varrone, Chem. Eur. J. 1998, 4, 2018-2030.
16. A. Arduini, A. Pochini, A. Secchi, Eur. J. Org. Chem. 2000, 2325-2334.
17. S. Smirnov, V. Sidorov, H. Pinkhassik, J. Havlicek, I. Stibor, Supramol. Chem. 1997, 8, 187-196.
18. V. Wendel, W. Abraham, Tetrahedron Lett. 1997, 38, 1177-1180.
19. L. Grubert, D. Jacobi, W. Abraham, J. Prakt. Chem. 1999, 341, 620-630.
20. D. Jacobi, W. Abraham, U. Pischel, L. Grubert, W. Schnabel, J. Chem. Soc., Perkin Trans 2 1999, 1695-1702.
21. A. Shivanyuk, E. F. Paulus, V. Böhmer, Angew. Chem. 1999, 111, 3091;
22. Angew. Chem. Int. Ed.1999, 38, 2906-2909.
23. J. Masrans, J. de Mendoza, M. Pons, P. Prados, J. Org. Chem. 1997, 62, 4518-4520.
24. C. D. Gutsche, L. J. Bauer, J. Am. Chem. Soc. 1985, 107, 6052-6063.
25. H. Günther, M. Görlitz, H. H. Hinrichs, Tetrahedron 1968, 24, 5665-5676.
26. S. Shinkai, Tetrahedron 1993, 49, 8933-8968.
27. A. Ikeda, H. Tsuzuki, S. Shinkai, J. Chem. Soc., Perkin Trans. 2 1994, 2073-2080.
28. A. Arduni, S. Fanni, G. Manfredi, A. Pochini, R. Ungaro, A. R. Sicuri, F. Ugozzoli, J. Org. Chem. 1995, 60, 1448-1457.
29. A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713-1734.
30. J. Scheerder, R. H. Vreeskamp, J. F. J. Engbersen, W. Verboom, J. P. M. van Duynhoven, D. N. Reinhoudt, J. Org. Chem. 1996, 61, 3476-3481.
31. M. Larsen, F. C. Krebs, N. Harrit, M. Jorgensen, J. Chem. Soc., Perkin Trans. 2 1999, 1749-1757.
32. F. Uggozzoli, G. Andreetti, J. Incl. Phenom. Mol. Rec. Chem. 1992, 13, 337-348.
33. H.-J. Schneider, A. Yatsimirsky, Principles and Methods in Supramolecular Chemistry, Wiley, Chichester, 2000.
34. W. Abraham; B. Dreher, D. Kreysig, N. A. Sadovskij, M. G. Kuzmin, J. Prakt. Chem. 1987, 329, 569-578.
35. M. Lämsa, T. Kuokkanen, J. Jalonen, O. Virtanen, J. Phys. Org. Chem. 1995, 8, 377-384.
36. M. A. Battiste, M. Couch, W. Rehberg, J. Phys. Chem. 1977, 81, 64-67.
37. U. Pischel, W. Abraham, W. Schnabel, U. Müller, J. Chem. Soc., Chem. Commun. 1997, 1383-1384.
38. V. Kharlanov, W. Abraham, unpublished results.
39. R. S. Macomber, J. Chem. Educ. 1992, 69, 375-378.
40. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallocraphic Data Centre as supplementary publication no. CCDC-151853 (10), -151864 (21), -151855 (37). Copies of the data can be obtained free of charge on applicaton to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
41. G.M. Sheldrick, SHELXL-97, Universität Göttingen, 1997.
42. Z.-C. Ho, M.-C. Shu, L.-G. Lin, Tetrahedron 1996, 52, 13189-13200.
43. C. D. Gutsche, L.-G. Ling, Tetrahedron 1986, 42, 1633-1640.
44. K. A. See, F. R. Fronczek, W. H. Watson, R. P. Hashyap, C. D. Gutsche, J. Org. Chem. 1991, 56, 7256-7268.
45. J.-D. van Loon, A. Arduini, L. Coppi, W. Verboom, A. Pochini, R. Ungaro, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1990, 55, 5639-5646.
46. L. C. Groenen, B. H. M. Ruel, A. Casnati, W. Verboom, A. Pochini, R. Ungaro, D. N. Reinhoudt, Tetrahedron 1991, 47, 8379-8384.
47. C. Jutz, F. Voithenleitner, Chem. Ber. 1964, 97, 29-48.