Rigid Tetranitroresorcinarenes

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1555-1558

  Shivanyuk, Alexander ^a   Far, Adel Rafai ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 FLUORO 2,4 DINITROBENZENE; 1,5 DIFLUORO 2,4 DINITROBENZENE; 1,5-DIFLUORO-2,4-DINITROBENZENE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NITRO DERIVATIVE; RESORCINOL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTROSPRAY MASS SPECTROMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

ALKYLATION; CRYSTALLOGRAPHY, X-RAY; DINITROFLUOROBENZENE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRO COMPOUNDS; RESORCINOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0037007720     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025725h     Document Type: Article

References (31)

1. For reviews see: (a) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield J., Vicens, J., Saadioui, M., Eds.; Kluwer Academic Publishers: Dordrecht Boston, London, 2001.
2. (b) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests: Stoddart, F., Ed.; The Royal Society of Chemistry: London, 1994.
3. (c) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
4. (d) Rudkevich, D. M.; Rebek, J. Jr. Eur. J. Org. Chem. 1999, 1991-2005.
5. (e) Higler, I.; Boerrigter, H.; Verboom, W.; Kooijman, H.; Spek, A. L.; Reinhoudt, D. N. Eur. J. Org. Chem. 1998, 1597-1607.
6. (a) Verboom, W.; Durie, A.; Egberink, R. J. M.; Asfari, Z.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 1313-1316.
7. (b) Jakobi, R. A.; Böhmer V.; Grüttner, C.; Kraft, D.; Vogt, W. New. J. Chem. 1996, 20, 493-498.
8. (a) Jakobi, R. A.; Böhmer, V.; Grüttner, C.; Kraft, D.; Vogt. W. New J. Chem. 1996, 20, 493-498.
9. (b) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329.
10. Sheerder, J.; van Duynhoven, J. P. M.; Engbersen, J. F.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1090-1093.
11. (a) Rudkevich, D. M.; Hilmersson, G.; Rebek, J. Jr. J. Am. Chem. Soc. 1998, 120, 12216-12225.
12. (b) Haino, T.; Rudkevich, D. M.; Shivanyuk, A.; Rissanen, K.; Rebek, J., Jr. Chem. Eur. J. 2000, 6, 3797-3805.
13. (a) Kalchenko, V. I.; Rudkevich, D. M.; Shivanyuk, A. N.; Tsymbal, I. F.; Pirozhenko, V. V.; Markovsky, L. N. Zh. Obshch. Khim. 1994, 64, 731-742; Russ. J. Gen. Chem. 1994, 64, 663-672.
14. (a) Kalchenko, V. I.; Rudkevich, D. M.; Shivanyuk, A. N.; Tsymbal, I. F.; Pirozhenko, V. V.; Markovsky, L. N. Zh. Obshch. Khim. 1994, 64, 731-742; Russ. J. Gen. Chem. 1994, 64, 663-672.
15. (b) Lukin, O. V.; Pirozhenko, V. V.; Shivanyuk, A. N. Tetrahedron Lett. 1995, 36, 7725-7728.
16. (c) Lukin, O.; Shivanyuk, A.; Pirozhenko, V. V.; Tsymbal, I. F.; Kal'chenko, V. I. J. Org. Chem., 1998, 63, 9510-9516.
17. (d) Shivanyuk, A.; Paulus, E. F.; Böhmer, V.; Vogt, W. Org. Chem. 1998, 63, 6448-6449.
18. (a) Shivanyuk, A.; Paulus, E. F.; Rissanen, K.; Kolehmainen, E.; Böhmer, V. Chem. Eur. J. 2001, 7, 1944-1951.
19. (b) Shivanyuk, A. Chem. Commun. 2001, 1472-1473.
20. PCMODEL is distributed by Serena Software, Dr. Kevin E. Gilbert, P.O. 3076, Bloomington, IN 47402.
21. For bridging of resorcarene tetrasulfonates through the aminomethylation with suitable diamines, see: (a) Shivanyuk, A.; Schmidt, C.; Böhmer, V.; Paulus, E. F.; Lukin, O. V.; Vogt, W. J. Am. Chem. Soc. 1998, 120, 4319-4326.
22. (b) Arnott, G.; Bulman Page, P. C.; Heaney, H.; Hunter, R.; Sampler, E. P. Synlett 2001, 412-414.
23. -1): 1745, 1619, 1600, 1532, 1490.
24. -3.
25. (a) Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467.
26. (b) Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures: Universität Göttingen: Göttingen, Germany, 1997.
27. For a recent review, see: König, B.; Fonseca, M. H. Eur. J. Inorg. Chem. 2000, 2303-2310.
28. The reaction of resorcinol and 1,3-dichloro-4,6-dinitrobenzene in 1:1 ratio was reported to give corresponding oxygen-bridged calix[4]arene in low yield; however, no crystallographic studies were undertaken on that compound: (a) Sommer, N.; Staab, H. A. Tetrahedron Lett. 1966, 2837-2841.
29. (b) Lehmann, F. Tetrahedron 1974, 30, 727-733.
30. (c) Boros, E. E.; Andrews, C. W.; Davis, A. O. J. Org. Chem. 1996, 61, 2553-2555.
31. (d) Bottino, F.; Foti, S.; Pappalardo, S. Tetrahedron 1976, 32, 2567-2570.