Aggregates of calix[4]arenes based on the 2,6-diaminotriazine · imide system

Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands

Volumn 115, Issue 7-8, 1996, Pages 363-370

  Vreekamp, Remko H ^a   Verboom, Willem ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748817022     PISSN: 01650513     EISSN: None     Source Type: Journal    
DOI: 10.1002/recl.19961150705     Document Type: Article

References (50)

1. See for instance: a J.S. Lindsey, New J. Chem. 15, 153 (1991);
2. b G.M. Whitesides, E.K. Simanek, J.P. Mathias, C.T. Seto, N.C. Donovan, M. Mammen and D.M. Gordon, Acc. Chem. Res. 28, 37 (1995).
3. For a recent review see: V. Böhmer, Angew. Chem. Int. Ed. Engl. 34, 713 (1995).
4. K. Fujimoto and S. Shinkai, Tetrahedron Lett. 35, 2915 (1994).
5. J.-D. van Loon, R.G. Janssen, W. Verboom and D.N. Reinhoudt, Tetrahedron Lett. 33, 5125 (1992).
6. G.G. Hammes and A.C. Park, J. Am. Chem. Soc. 91, 956 (1969).
7. All association constants given are in chloroform at 298K unless stated otherwise.
8. K. Koh, K. Araki and S. Shinkai, Tetrahedron Lett 35, 8255 (1994).
9. R.H. Vreekamp, W. Verboom and D.N. Reinhoudt, J. Org. Chem. in press.
10. A. Arduini, M. Fabbi, M. Mantovani, L. Mirone, A. Pochini, A. Secchi and R. Ungaro, J. Org. Chem. 69, 1454 (1995).
11. R.H. Vreekamp, J.P.M. van Duynhoven, M. Hubert, W. Verboom and D.N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 35, 1215 (1996).
12. T.R. Kelly and M.P. Maguire, J. Am. Chem. Soc. 109, 6549 (1987).
13. a A.D. Hamilton and D. van Engen, J. Am. Chem. Soc. 109, 5035 (1987);
14. b A.D. Hamilton and D. Little, J. Chem. Soc., Chem. Commun. 297 (1990).
15. H.-J. Schneider, R.K. Juneja and S. Simova, Chem. Ber. 122, 1211 (1989).
16. a S.-K. Chang and A.D. Hamilton, J. Am. Chem. Soc. 110, 1318 (1988);
17. b T.K. Park, J. Schroeder and J. Rebek, Jr., J. Am. Chem. Sec. 113, 5125 (1991);
18. c I. Willner, J. Rosengaus and S. Biali, Tetrahedron Lett. 33, 3805 (1992);
19. d T.K. Park, Q. Feng and J. Rebek, Jr., J. Am. Chem. Soc. 114, 4529 (1992);
20. e J.-D. van Loon, J.F. Heida, W. Verboom and D.N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 111, 353 (1992).
21. K. Williams, B. Askew, P. Ballester, C. Buhr, K. Jeong, S. Jones and J. Rebek, Jr., J. Am. Chem. Soc. 111, 1090 (1989).
22. Y. Kyogoku, R.C. Lord and A. Rich, Proc. Natl. Acad. Sci. USA 57, 250 (1967).
23. J. Pranata, S.G. Wierschke and W.L. Jorgensen, J. Am. Chem. Soc. 113, 2810 (1991).
24. A. Harriman. D.J. Magda and J.L. Sessler, J. Phys. Chem. 95, 1530 (1991).
25. Y. Kyogoku, R.C. Lord and A. Rich, Biochem. Biophys. Acta 53, 884 (1969).
26. J.-D. van Loon, A. Arduini, L. Coppi, W. Verboom, A. Pochini, R. Ungaro, S. Harkema and D.N. Reinhoudt, J. Org. Chem. 55, 5639 (1990).
27. S. Shinkai, T. Nagasaki, K. Iwamoto, A. Ikeda and G.-X. He, Bull. Chem. Soc. Jpn. 64, 381 (1991).
28. D.J. Brown and T. Teitel, J. Chem. Soc. 3204 (1964).
29. C.D. Gutsche and P.F. Pagoria, J. Org. Chem. 50, 5795 (1985).
30. J.K. Simons and M.R. Saxton, Org. Synth. 33, 13 (1953).
31. Heating of nitriles in alkaline alcoholic medium has been proven to be an effective method for converting these compounds into the corresponding amides: J.H. Hall and M. Gisler, J. Org. Chem. 41, 3769 (1976).
32. R. Ruggieri, Giom. Med. Militare 107, 4 (1957);
33. Chem. Abstr. 53, 21792a (1959).
34. I. Horman and B. Dreux, Helv. Chim. Acta 67, 754 (1984).
35. M. Gallant, M.T.P. Viet and J.D. Wuest, J. Org. Chem. 56, 2284 (1991).
36. Y. Kuroda, J.M. Lintuluoto and H. Ogoshi, Tetrahedron Lett. 35, 3729 (1994).
37. S.C. Hirst and A.D. Hamilton, Tetrahedron Lett. 31, 2401 (1990).
38. M.S. Goodman and S.D. Rose, J. Am. Chem. Soc. 113, 9380 (1991).
39. o of 5.7 kcal/mol.
40. See for instance: a M. Conner, V. Janout and S.L. Regen, J. Am. Chem. Soc. 113, 9670 (1991);
41. b J. Scheerder, R.H. Vreekamp, J.F.J. Engbersen, W. Verboom, J.P.M. van Duynhoven and D.N. Reinhoudt, J. Org. Chem. 61, 3476 (1996);
42. c W. Verboom, R.H. Vreekamp, P.J. Bodewes, S. Harkema and D.N. Reinhoudt, Reel. Trav. Chim. Pays-Bas accepted for publication.
43. 11-13 for related systems, in our case the complexation may also be very weak.
44. 3 are obtained for all precursors of 16.
45. Upon inverting the vial containing the clear tertiary mixture, the contents moved downward very slowly.
46. K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama and H. Shirai, J. Chem. Soc., Chem. Commun. 1382 (1993).
47. To the best of our knowledge, only Shinkai et al. have reported on calixarene-based gelators of organic fluids. Calixarenes, having long acyl groups at the para positions, give gels in various organic solvents which are based on intermolecular C = O....HO hydrogen bonding: M. Aoki, K. Nakashima, H. Kawabata, S. Tsutsui and S. Shinkai, J. Chem. Soc., Perkin Trans. 2 347 (1993).
48. J.-M. Lehn, M. Mascal, A. DeCian and J. Fischer, J. Chem. Soc., Chem. Commun. 479 (1990).
49. Formation of hydrogen-bonded strands through the interaction of 15b with 4 would only be expected if both had divergent hydrogen-bonding groups. Earlier we had seen that that does not appear to be the case for 4.
50. C.D. Gutsche and M. Iqbal, J. Org. Chem. 68, 234 (1989).