Wide rim urethanes derived from calix[4]arenes: Synthesis and self-assembly

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3429-3434

  Cao, Yudong ^a   Vysotsky, Myroslav O ^a   Böhmer, Volker ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; DIMERS; HYDROGEN BONDS; MIXTURES; POSITIVE IONS; SYNTHESIS (CHEMICAL); UREA;

HETERODIMERIZATION; TETRAETHYLAMMONIUM CATIONS; URETHANE DERIVATIVES;

SELF ASSEMBLY;

5,11,17 TRITOLYLUREA 23 TOLYLCARBAMOYLOXY 25,26,27,28 TETRAPENTYLOXYCALIX[4]ARENE; 5,17 DITOLYLUREA 11,23 DITOLYLCARBAMOYLOXY 25,26,27,28 TETRAPENTYLOXYCALIX[4]ARENE; BENZENE; CALIXARENE; TETRYLAMMONIUM; UNCLASSIFIED DRUG; UREA DERIVATIVE; URETHAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DIMERIZATION; HYDROGEN BOND; MOLECULAR DYNAMICS; SYNTHESIS;

EID: 33646239641     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0524369     Document Type: Article

References (26)

1. Rebek, J., Jr. Chem. Commun. 2000, 637-643.
2. Shimizu, K.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403-12407.
3. Hamann, B. C.; Shimizu, K.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329.
4. Vysotsky, M. O.; Böhmer, V. Org. Lett. 2000, 2, 3571-3574.
5. Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. Chem. Commun. 1996, 2533-2534.
6. One of the referees of ref 4 even suggested that there is no hydrogen bond because the NH group must be in this distance as a result of the overall geometry of the capsule.
7. Thondorf, I.; Broda, F.; Rissanen, K.; Vysotsky, M. O.; Böhmer, V. J. Chem. Soc., Perkin Trans. 2 2002, 1796-1800.
8. p-Nitrophenyl urethanes of calix[4]arenes, in which the other NH group is replaced by O, were prepared and used for the synthesis of tetraureas. They do not show self-association to dimers.
9. Komori, T.; Shinkai, S. Chem. Lett. 1992, 901-904.
10. Mascal, M.; Warmuth, R.; Naven, R. T.; Edwards, R. A.; Hursthouse, M. B.; Hibbs, D. E. J. Chem. Soc., Perkin Trans, 1 1999, 1, 3435-3441.
11. Arduini, A.; Mirone, L.; Paganuzzi, D.; Pinalli, A.; Pochini, A.; Secchi, A.; Ungaro, R. Tetrahedron 1996, 32, 6011-6018.
12. Mascal, M.; Naven, R. T.; Warmuth, R. Tetrahedron Lett. 1995, 36, 9361-9364.
13. Brody, M. S.; Schalley, C. A.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1640-1644.
14. Kenis, P. J. A.; Noordman, O. F. J.; Schönherr, H.; Kerver, E. G.; Snellink-Rüel, B. H. M.; van Hummel, G. J.; Harkema S.; van der Vorst, C. P. J. M.; Hare, J.; Picken, S. J.; Engbersen, J. F. J.; van Hulst, N. F.; Vancso, G. J.; Reinhoudt, D. N. Chem.-Eur. J. 1998, 4, 1225-1234.
15. Budka, J.; Lhoták, P.; Michlová, V.; Stibor, I. Tetrahedron Lett. 2001, 42, 1583-1586.
16. Only the 1,3-isomer was synthesized and studied here, but the 1,2-isomer could be prepared analogously, as well as a mononitro-tri-hydroxy derivative.
17. Alternatively, it should be possible to acylate the hydroxy groups before the nitro groups are hydrogenated.
18. Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671-12672.
19. Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663.
20. For the synthesis of 13 and 14. see: Bogdan, A.; Vysotsky, M. O.; Wang, L.; Böhmer, V. Chem. Commun. 2004, 1268-1269.
21. Shivanyuk, A.; Saadioui, M.; Broda, F.; Thondorf, I.; Vysotsky, M. O.; Rissanen, K.; Kolehmainen, E.; Böhmer, V. Chem.-Eur. J. 2004, 10, 2138-2148.
22. A further splitting at lower temperature as a result of the directionality of the hydrogen-bonded belt is not discussed.
23. Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228-1234.
24. Vysotsky, M. O.; Pop, A.; Broda, F.; Thondorf, I.; Böhmer, V. Chem.-Eur. J. 2001, 7, 4403-4410.
25. Arnaud-Neu, F.; Barboso, S.; Böhmer, V.; Brisach, F.; Delmau, L.; Dozol, J.-F.; Mogck, O.; Paulus, E. F.; Saadioui, M.; Shivanyuk, A. Aust. J. Chem. 2003, 56, 1113-1120.
26. Ikeda, A.; Tsuzuki, H.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1994, 2073-2080.