Selective lower rim reactions of 5,17-upper rim-disubstituted calix[4]arenes

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2564-2568

  Sharma, Shiv Kumar ^a   Gutsche, C David ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343630752     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952013e     Document Type: Article

References (25)

1. Paper 45 in the series Calixarenes. For paper 44, cf. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1996, 61, 2511.
2. The term "calixarene" is variously employed in different contexts. In colloquial usage (as employed in the Discussion section), it implies the presence of hydroxyl groups. In the more precise and complete specification of a compound (as used in the Experimental Section), it implies only the basic skeleton to which the substituents, including the OH groups, are attached at positions designated by appropriate numbers as shown in the following structure. (Matrix Presented)
3. (a) Gutsche, C. D. Calixarenes in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989
4. (b) Calixarenes, A Versatile Class of Macrocyclic Compounds, Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991.
5. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
6. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 3-9.
7. Shinkai, S.; Tsubaki, T.; Sone, T.; Manabe, O. Tetrahedron Lett. 1985, 26, 3343. Shinkai, S.; Araki, K.; Tsubaki, T.; Arimura, T.; Manabe, O. J. Chem. Soc., Perkin Trans. 1 1987, 2297.
8. Shinkai, S.; Tsubaki, T.; Sone, T.; Manabe, O. Tetrahedron Lett. 1985, 26, 3343. Shinkai, S.; Araki, K.; Tsubaki, T.; Arimura, T.; Manabe, O. J. Chem. Soc., Perkin Trans. 1 1987, 2297.
9. No, K.; Noh, Y. Bull. Korean Chem. Soc. 1986, 7, 314.
10. Verboom, W ; Durie, A.; Egberink, R. J. M.; Asfari, Z.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 1313.
11. van Loon, J.-D.; Arduini, A.; Verboom, W.; Ungaro, R.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron Lett. 1989, 30, 2681. van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639.
12. van Loon, J.-D.; Arduini, A.; Verboom, W.; Ungaro, R.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron Lett. 1989, 30, 2681. van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639.
13. Kelderman, E.; Derhaeg, L.; Heesink, G. J. T.; Verboom, W.; Engbersen, J. F. J.; van Hulst, N. F.; Persoons, A.; Reinhoudt, D. N Angew. Chem., Int. Ed. Engl. 1992, 31, 1075.
14. Beer, P. D.; Gale, P. A.; Hesek, D. Tetrahedron Lett. 1995, 36, 767.
15. Dijkstra, P. J.; Brunink, J. A. J.; Bugge, K. E.; Reinhoudt, D. N.; Harkema, S.; Ungaro, R.; Ugozzoli, F.; Ghidini, E. J. Am. Chem. Soc. 1989, 111, 7567. Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783.
16. Dijkstra, P. J.; Brunink, J. A. J.; Bugge, K. E.; Reinhoudt, D. N.; Harkema, S.; Ungaro, R.; Ugozzoli, F.; Ghidini, E. J. Am. Chem. Soc. 1989, 111, 7567. Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783.
17. Attempts to prepare a dinitrocalix[4]arene by nitration of calix-[4]arene or its ethyl ether led to mixtures of the tetranitro and dinitro compounds (see Experimental Section).
18. 3 (50 equiv) was employed in very dilute solution, the product was the 1,3-alternate conformer, but the cone conformer was the major product when a more concentrated solution was used.
19. Gutsche, C. D.; Lin, L.-g. Tetrahedron 1986, 42, 1633.
20. Jaime, C.; deMendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372.
21. Verboom, W.; Datta, S.; Asfari, Z.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 5394.
22. Iqbal, M.; Mangiafico, T.; Gutsche, C. D. Tetrahedron 1987, 21, 4917.
23. 1H NMR resonance of the tert-butyl groups generally moves upfield from its position at δ 1.24 in the starting material.
24. 6 (40.0 ppm), or TMS (0.00 ppm) and also recorded at room temperature (20 ± 1°C). Microanalytical samples were dried for at least 48-72 h at 111°C (toluene) or at 140°C (xylene) at 1-2 mm, and the analyses were carried out by Desert Laboratories, Tucson, AZ. Solvent of crystallization was retained in some of the analytical samples and affected the elemental analysis. In such cases, best fits between the analytical values and appropriate increments of the solvents were used.
25. 6