Resorcinarenes as templates: A general strategy for the synthesis of large macrocycles

Journal of the American Chemical Society

Volumn 125, Issue 3, 2003, Pages 650-651

  Li, Xuehe ^a   Upton, Thomas G ^a   Gibb, Corinne L D ^a   Gibb, Bruce C ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHER; MACROCYCLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RESORCINARENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; REACTION ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 0037460139     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029116g     Document Type: Article

References (28)

1. Diederich, F., Stang, P. J., Eds. Templated Organic Synthesis; Wiley-VCH: Weiheim, 2000.
2. For recent reviews, see: (a) Bradshaw, J. S.; Izatt, R. M.; Bordunov, A. V.; Zhu, C. Y.; Hathaway, J. K. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier Science Ltd.: London, 1996; Vol 1, p 35-95.
3. (b) Bradshaw, J. S.; Izatt, R. M. Acc. Chem. Res. 1997, 30, 338-345.
4. (c) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529-2586.
5. For examples of template effects and the formation of crown ethers, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036. (b) Greene, R. N. Tetrahedron Lett. 1972, 1793-1796. (c) New Mandolini, L.; Reinhoudt, D. N.; De Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 22, 2067-2070. (d) Habata, Y.; Fujishiro, F.; Akabori, S. J. Chem. Soc., Perkin Trans. 1 1996, 9, 953-957. (e) Bowsher, B. R.; Rest, A. J. Inorg. Chem. Acta 1981, 53, L175-L176. (f) Wingfield, J. N. Inorg. Chim. Acta 1980, 45, L157-L159.
6. For examples of template effects and the formation of crown ethers, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036. (b) Greene, R. N. Tetrahedron Lett. 1972, 1793-1796. (c) New Mandolini, L.; Reinhoudt, D. N.; De Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 22, 2067-2070. (d) Habata, Y.; Fujishiro, F.; Akabori, S. J. Chem. Soc., Perkin Trans. 1 1996, 9, 953-957. (e) Bowsher, B. R.; Rest, A. J. Inorg. Chem. Acta 1981, 53, L175-L176. (f) Wingfield, J. N. Inorg. Chim. Acta 1980, 45, L157-L159.
7. For examples of template effects and the formation of crown ethers, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036. (b) Greene, R. N. Tetrahedron Lett. 1972, 1793-1796. (c) New Mandolini, L.; Reinhoudt, D. N.; De Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 22, 2067-2070. (d) Habata, Y.; Fujishiro, F.; Akabori, S. J. Chem. Soc., Perkin Trans. 1 1996, 9, 953-957. (e) Bowsher, B. R.; Rest, A. J. Inorg. Chem. Acta 1981, 53, L175-L176. (f) Wingfield, J. N. Inorg. Chim. Acta 1980, 45, L157-L159.
8. For examples of template effects and the formation of crown ethers, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036. (b) Greene, R. N. Tetrahedron Lett. 1972, 1793-1796. (c) New Mandolini, L.; Reinhoudt, D. N.; De Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 22, 2067-2070. (d) Habata, Y.; Fujishiro, F.; Akabori, S. J. Chem. Soc., Perkin Trans. 1 1996, 9, 953-957. (e) Bowsher, B. R.; Rest, A. J. Inorg. Chem. Acta 1981, 53, L175-L176. (f) Wingfield, J. N. Inorg. Chim. Acta 1980, 45, L157-L159.
9. For examples of template effects and the formation of crown ethers, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036. (b) Greene, R. N. Tetrahedron Lett. 1972, 1793-1796. (c) New Mandolini, L.; Reinhoudt, D. N.; De Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 22, 2067-2070. (d) Habata, Y.; Fujishiro, F.; Akabori, S. J. Chem. Soc., Perkin Trans. 1 1996, 9, 953-957. (e) Bowsher, B. R.; Rest, A. J. Inorg. Chem. Acta 1981, 53, L175-L176. (f) Wingfield, J. N. Inorg. Chim. Acta 1980, 45, L157-L159.
10. For examples of template effects and the formation of crown ethers, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036. (b) Greene, R. N. Tetrahedron Lett. 1972, 1793-1796. (c) New Mandolini, L.; Reinhoudt, D. N.; De Jong, F.; Tomassen, H. P. M. Tetrahedron Lett. 1979, 22, 2067-2070. (d) Habata, Y.; Fujishiro, F.; Akabori, S. J. Chem. Soc., Perkin Trans. 1 1996, 9, 953-957. (e) Bowsher, B. R.; Rest, A. J. Inorg. Chem. Acta 1981, 53, L175-L176. (f) Wingfield, J. N. Inorg. Chim. Acta 1980, 45, L157-L159.
11. Gibson, H. G.; Bheda, M. C.; Engen, P.; Shen, Y. X.; Sze, J.; Zhang, H.; Gibson, M. D.; Delaviz, Y.; Lee, S.-H.; Liu, S.; Wang, L.; Nagvekar, D.; Rancourt, J.; Taylor, L. T. J. Org. Chem. 1994, 59, 2186-2196.
12. (a) Masci, B. Tetrahedron 1989, 45(7), 2201-2212.
13. (b) Kime, D. E.; Norymberski, J. J. Chem. Soc., Perkin Trans. 1 1977, 1048-1052.
14. (a) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663-2704.
15. (b) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, 1994.
16. 2Ph).
17. (a) Xi, H.; Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. Chem. Commun. 1998, 1743-1744.
18. (b) Xi, H.; Gibb, C. L. D.; Gibb, B. C. J. Org. Chem. 1999, 64, 9286-9288.
19. (c) Green, J. O.; Baird, J.-H.; Gibb, B. C. Org. Lett. 2000, 2, 3845-3848.
20. Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. J. Am. Chem. Soc. 2001, 123, 5849-5850.
21. Laugherey, Z.; Gibb, C. L. D.; Gibb, B. C. Chem.-Eur. J., in press.
22. The reaction between 5 and 3,5-dihydroxybenzyl alcohol required more concentrated conditions than those used in the synthesis of 6a-c. As a result, the amount of polymer increased at the expense of 6d. We have also tried bridging with 3,5-dihydroxy benzoic acid and 3,5-dihydroxy benzaldehyde. The former gave no reaction, and the latter gave a very small amount of partially bridged intermediates.
23. 3 gave lower yields.
24. 2 resulted in the formation of an inseparable mixture of macrocycles arising from Br/Cl exchange.
25. Gibb, C. L. D.; Li, X.; Gibb, B. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4857-4862.
26. (a) Konishi, H.; Ohata, K.; Morikawa, O.; Kobayashi, K. Chem. Commun. 1995, 309-310.
27. (b) Konishi, H.; Nakamura, T.; Ohata, K.; Morikawa, O.; Kobayashi, K. Tetrahedron Lett. 1996, 37, 7383-7386.
28. Naumann, C.; Romàn, E.; Peinador, C.; Ren, T.; Patrick, B. O.; Kaifer, A. E.; Sherman, J. C. Chem.-Eur. J. 2001, 7, 1637-1645.