Upper rim substitution of calix[4]arenes via their upper rim A,C dinitro compounds

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 998-1003

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

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEALKYLATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033525044     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980903z     Document Type: Article

References (17)

1. Paper no. 50 in a series entitled Calixarenes. For paper no. 49 cf.: Xie, D.; Gutsche, C. D. J. Org. Chem. 1999, 64, 9270.
2. Gutsche, C. D.; Iqbal, M. Org. Synth. 1990, 68, 234.
3. (a) Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1998.
4. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilties. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
5. (c) Gutsche, C. D. Calixarenes. Aldrichimica Acta 1995, 28, 3-9.
6. (d) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991.
7. (e) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
8. Sharma, S. K.; Gutsche, C. D. J. Org. Chem. 1996, 61, 2564.
9. 3 in MeCN at 0°C that is stated to give pure p-nitrocalix[4]arene, p-nitrocalix[6]arene, and p-nitrocalix[8]arene in yields of 84, 89, and 84%, respectively. Attempts in our laboratories to reproduce these results, however, have yielded mixtures in all cases, leading to considerably lower yields of pure p-nitrocalix[4]arene in the first case and to no isolable product in the other two cases. The procedure for generating p-nitrocalix[4]arene and p-nitrocalix[8]arene were studied under a variety of conditions in which the ratio of reactants, the temperature, and the time of reaction were varied. Under none of these conditions could the reported data be reproduced.
10. (a) 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.
11. (b) van Loon, J.-D.; Arduini, A.; Verboom, W.; Ungaro, R.; van Hummel, G. J.; Harkema, S. Reinhoudt, D. N. Tetrahedron Lett. 1989, 30, 2681.
12. (c) Verboom, W.; Durie, A.; Egberink, R. J. M.; Asfari, Z.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 1313.
13. (d) Timmerman, P.; Verboom, W.; Reinhoudt, D. N.; Arduini, A.; Grandi, S.; Sicuri, A. R.; Pochini, A.; Ungaro, R. Synthesis 1994, 185.
14. Yang, X.; McBranch, D.; Swanson, B.; Li, DeQuan Angew. Chem., Int. Ed. Engl. 1996, 35, 538.
15. Xie, D.; Gutsche, C. D. J. Org Chem. 1999, 64, 9270.
16. Jøorgensen, M.; Larsen, M.; Sommer-Larsen, P.; Petersen, W. B.; Eggert, H. J. Chem. Soc., Perkin Trans, 1 1997, 2851.
17. 6 at δ 3.4 ppm.