Synthesis and reactivity of calix[4]arene-based copper complexes

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9270-9278

  Xie, Dejian ^a   Gutsche, C David ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIX(4)ARENE; CALIXARENE; CHELATE; COPPER COMPLEX; METHANOL; OXYGEN; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; COMPLEX FORMATION; OXIDATION; REDUCTION; SYNTHESIS;

EID: 0032509382     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981038l     Document Type: Article

References (38)

1. Paper No. 49 in the series entitled "Calixarenes". For paper no. 48, see: Wang, J.; Gutsche, C. D. J. Am. Chem. Soc. 1998, 120, 12226-12231.
2. For general reviews, cf: (a) Karlin, K. D.; Tyeklár, Z.; Zuberbühler, A. D. In Bioinorganic Catalysis; Reedijk, J., Ed.; Marcel Dekker: New York, 1992; Chapter 9. (b) Sorrell, T. N. Tetrahedron 1989, 45, 3.
3. For general reviews, cf: (a) Karlin, K. D.; Tyeklár, Z.; Zuberbühler, A. D. In Bioinorganic Catalysis; Reedijk, J., Ed.; Marcel Dekker: New York, 1992; Chapter 9. (b) Sorrell, T. N. Tetrahedron 1989, 45, 3.
4. For recent reviews, cf: (a) Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737. (b) Karlin, K. D., Kaderli, S.; Zuberbühler, A. D. Acc. Chem. Res. 1997, 30, 139. (c) Tolman, W. B. Acc. Chem. Res. 1997, 30, 227.
5. For recent reviews, cf: (a) Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737. (b) Karlin, K. D., Kaderli, S.; Zuberbühler, A. D. Acc. Chem. Res. 1997, 30, 139. (c) Tolman, W. B. Acc. Chem. Res. 1997, 30, 227.
6. For recent reviews, cf: (a) Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737. (b) Karlin, K. D., Kaderli, S.; Zuberbühler, A. D. Acc. Chem. Res. 1997, 30, 139. (c) Tolman, W. B. Acc. Chem. Res. 1997, 30, 227.
7. Cf. refs 1-6 in Karlin, K. D.; Nasir, M. S.; Cohen, B. I.; Cruse, R. W.; Kaderli, S.; Zuberbühler, A. D. J. Am. Chem. Soc. 1994, 116, 1324.
8. For reviews, cf: (a) Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1998. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilties. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. (c) Gutsche, C. D. Calixarenes. Aldrichimica Acta 1995, 28, 3-9. (d) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands 1991. (e) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
9. For reviews, cf: (a) Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1998. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilties. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. (c) Gutsche, C. D. Calixarenes. Aldrichimica Acta 1995, 28, 3-9. (d) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands 1991. (e) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
10. For reviews, cf: (a) Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1998. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilties. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. (c) Gutsche, C. D. Calixarenes. Aldrichimica Acta 1995, 28, 3-9. (d) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands 1991. (e) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
11. For reviews, cf: (a) Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1998. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilties. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. (c) Gutsche, C. D. Calixarenes. Aldrichimica Acta 1995, 28, 3-9. (d) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands 1991. (e) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
12. For reviews, cf: (a) Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1998. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilties. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. (c) Gutsche, C. D. Calixarenes. Aldrichimica Acta 1995, 28, 3-9. (d) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands 1991. (e) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
13. Sorell, T. N.; Malachowski, M. R.; Jameson, D. L. Inorg. Chem. 1982, 21, 3251.
14. Brady, L. E.; Freifelder, M.; Stone, G. R. J. Org. Chem. 1961, 26, 4757.
15. (a) Alam, I.; Sharma, S. K.; Gutsche, C. D. J. Org. Chem. 1994, 59, 3716.
16. (b) Sharma, S. K.; Alam, I.; Gutsche, C. D. Synthesis 1995, 1089.
17. Longer reaction times result in the formation of additional compounds, presumably the result of reduction of the 3,5-dimethlyl pyrazole ring. The preferred procedure for this reaction uses a large excess of diborane to force the reduction to go to completion but a short reaction time at room temperature to avoid over reduction.
18. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1995, 60, 6070.
19. Xie, D.; Gutsche, C. D. J. Org. Chem. 1997, 62, 2280.
20. Martens, C. F.; Schenning, A. P. H. J.; Feiters, M. C.; Berens, H. W.; van der Linden, J. G. M.; Admiraal, G.; Beurskens, P. T.; Kooijman, H.; Spek. A. L.; Nolte, J. M. Inorg. Chem. 1995, 19, 4735.
21. Almi, M.; Arduini, A.; Casnati, A.; Pochini, A.; Ungaro, R. Tetrahedron 1989, 45, 2117.
22. This reaction is easily followed by the color of the solution, reduction resulting in the green solution (Cu(II) species) changing to colorless or pale yellow (Cu(I) species). Also see refs 6 and 7.
23. Martens, C. F.; Schenning, A. P. H. J.; Klein Gebbink, R. J. M.; Feiters, M. C.; van der Linden, J. G. M.; Heck, J.; Nolte, R. J. M. J. Chem. Soc., Chem. Commun. 1993, 88.
24. Martens, C. F.; Klein Gebbink, R. J. M.; Feiters, M. C.; Nolte, R. J. M. J. Am. Chem. Soc. 1994, 116, 5667.
25. Kubas, G. J. Inorg. Synth. 1979, 19, 90.
26. (a) Kitajima, N.; Koda, T.; Hashimoto, S.; Kitagawa, T.; Morooka, Y. J. Chem. Soc. Chem. Commun. 1988, 151.
27. (b) Kitajima, N.; Fujisawa, K.; Moro-oka, Y.; Toriumi, K. J. Am. Chem. Soc. 1989, 111, 8975.
28. (c) Kitajima, N.; Koda, T.; Iwata, Y.; Moro-oka, Y. Ibid. 1990, 112, 8833.
29. (d) Kitajima, N.; Fujisawa, K.; Fujimoto, C.; Moro-oka, Y.; Hashimoto, S.; Kitagawa, T.; Toriumi, K.; Tatsumi, K.; Nakamura, A. Ibid. 1992, 114, 1277.
30. (a) Sorell, T. N.; Malachowski, M. R.; Jameson, D. L. Inorg. Chem. 1982, 21, 3251.
31. (b) Sorell, T. N.; Jameson, D. L.; O'Connor, C. J. Ibid. 1984, 23, 190.
32. (c) Sorell, T. N.; Vankai, V. A.; Garrity, M. L. Ibid. 1991, 30, 207.
33. Mahapatra, S.; Halfen, J. A.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11575.
34. Itoh, S.; Kondo, T.; Komatsu, M.; Ohshiro, Y.; Li, C.; Kanehisa, N.; Kai, Y.; Fukuzumi, S. J. Am. Chem. Soc. 1995, 117, 4714.
35. Itoh, S.; Nakao, H.; Berreau, L. M.; Kondo, T.; Komatsu, M.; Fukazumi, S. J. Am. Chem. Soc. 1998, 120, 2890.
36. We are indebted to Dr. Lisa Berreau, working in the laboratories of Professor William B. Tolman at the University of Minnesota, for investigating the spectroscopic properties of the complexes generated from calixarenes 22 and 24. Although the slow formation of green solutions was observed, characterized by a broad absorption centered at ca. 660 nm, no evidence for the existence of dioxygen complexes at -76 °C in THF solution was revealed. Dr. Berreau suggests that 34 might adopt a geometry upon metal binding in which steric hindrance at the metal center is reduced compared with the systems of Karlin and Itoh, resulting in a highly reactive (thermally unstable) complex that is not observable at the temperatures employed.
37. Andreetti, G. D.; Ungaro, R.; Pochini, A. J. Chem. Soc., Chem. Commun. 1979, 1005.
38. 13C NMR spectra were recorded on a Varian XL-300 spectrometer at 300 and 75 MHz, respectively. Analytical samples were dried in a drying pistol under vacuum for at least 36 h. Microanalyses were performed by Desert Laboratories, Tucson, AZ. Thin-layer chromatography (TLC) was carried out on Analtech silica gel plates (absorbant thickness 250 μm) containing a fluorescent indicator. Column chromatography was carried out with J. T. Baker silica gel no. JT7042-2 (40-64 μm particles) on columns filled to a height of ca. 6 in. Elution rates were 2 in./min. Mass spectral determinations were carried out by the Washington University Re-source for Biomedical and Bio-organic Mass Spectrometry, St. Louis, MO.