Synthesis of the tripodal-amine capped benzo crown p-tert-butylcalix[4]arene and its host-guest chemistry

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3985-3988

  Tuntulani, Thawatchai ^a   Ruangpornvisuti, Vithaya ^a   Tantikunwatthana, Nonglak ^a   Ngampaiboonsombut, Onanong ^a   Seangprasertkij Magee, Ratana ^a   Asfari, Zouhair ^b   Vicens, Jacques ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 TERT BUTYLCALIX[4]ARENE; CALIXARENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

ARENE;

EID: 0030965874     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00738-7     Document Type: Article

References (19)

1. Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, 1995, pp 271.
2. Lehn, J.-M. Acc. Chem. Res. 1978, 11, 49.
3. Dietrich, B.; Guilhem, J.; Lehn, J.-M.; Pascard, C.; Sonveaux, E. Helvetica Chimica Acta 1984, 67, 91.
4. Lehn, J.-M. Pure & Applied Chem. 1980, 52, 2441.
5. Lhotak, P.; Shinkai, S. J. Synth. Org. Chem. Jpn. 1995, 53, 41.
6. Bohmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713.
7. Pochini, A.; Ungarro, R. In Comprehensive Supramolecular Chemistry; F. Vogtle, Ed.; Pergamon Press: 1996; Vol. 2; pp 103.
8. Seangprasertkij, R.; Asfari, Z.; Arnuad, F.; Vicens, J. J. Org. Chem. 1994, 59, 1741.
9. 2O-); 5.20 (1H, s, ArOH); 6.32-7.85 (20H, m, aromatic protons); 9.75 and 10.41 (1H and 2H, s each, -Ar(C=O)H). FAB MS (m/z): 1092.5.
10. 2O); 5.30 (1H, s, -ArOH); 6.42-7.90 (20H, m, aromatic protons); 8.82 and 8.92 (1H and 2H, s each, -CH=N-). FAB MS (m/z): 1185.7.
11. 11): C, 65.69; H, 8.44; N, 3.78. Found: C, 65.61; H, 7.87; N, 3.97. FAB MS (m/z): 1191.7.
12. 2-). FAB MS (m/z): 1191.7.
13. The protonation constants of 6 were estimated by the Superquad computer program: Gans, P.; Sabatini, A.; Vacca, A. J. Chem. Soc., Dalton Trans. 1985, 1195. The deprotonation constant of methanol at 25°C was calculated to be log K = -16.7.
14. Motekaitis, R. J.; Martell, A. E.; Lehn, J.-M.; Watanabe, E.-I. Inorg. Chem. 1982, 21, 4253.
15. 3OD (1 mL) were then added to the ligand solution in each tube by varying the ratio of Zn(II):6 from 0.5:1 to 3:1.
16. Pothsree, T.; Seangprasertkij-Magee, R.; Tuntulani, T. J. Incl. Phenom. 1997 in press.
17. Seangprasertkij, R.; Asfari, Z.; Vicens, J. J. Incl. Phenom. 1994, 17, 111.
18. 2 solution (5 mL) of 6 (0.100g, 0.084 mmol). The reaction was allowed to stir at room temperature for 48 h. White solids precipitated from the reaction. The solvent volume was subsequently reduced, and white solids were separated by filtration and washed with diethylether. (0.061 g, 51%).
19. The proton signals due to tert-butyl groups appear at 0.53, 0.60, 0.65, 0.67, 1.03, 1.13, 1.17 and 1.19 ppm.