Practical synthesis of selectively functionalized cavitands

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 602-605

  Irwin, Jacob L ^a   Sherburn, Michael S ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

RESORCINOL DERIVATIVE;

ARTICLE; AUSTRALIA; COVALENT BOND; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034723305     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991185z     Document Type: Article

References (24)

1. Cram, D. J. Science 1983, 219, 1177-1183. Cram, D. J.; Cram, J. M. In Container Molecules and their Guests; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; Royal Society of Chemistry: Cambridge, 1994; Vol. 4.
2. Cram, D. J. Science 1983, 219, 1177-1183. Cram, D. J.; Cram, J. M. In Container Molecules and their Guests; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; Royal Society of Chemistry: Cambridge, 1994; Vol. 4.
3. Recent examples: Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Org. Chem. 1999, 64, 4555-4559. Watanabe, S.; Goto, K.; Kawashima, T.; Okazaki, R. Tetrahedron Lett. 1999, 40, 3569-3572. Boerrigter, H.; Tomasberger, T.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1999, 665-674. Duzamet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788.
4. Recent examples: Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Org. Chem. 1999, 64, 4555-4559. Watanabe, S.; Goto, K.; Kawashima, T.; Okazaki, R. Tetrahedron Lett. 1999, 40, 3569-3572. Boerrigter, H.; Tomasberger, T.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1999, 665-674. Duzamet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788.
5. Recent examples: Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Org. Chem. 1999, 64, 4555-4559. Watanabe, S.; Goto, K.; Kawashima, T.; Okazaki, R. Tetrahedron Lett. 1999, 40, 3569-3572. Boerrigter, H.; Tomasberger, T.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1999, 665-674. Duzamet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788.
6. Recent examples: Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Org. Chem. 1999, 64, 4555-4559. Watanabe, S.; Goto, K.; Kawashima, T.; Okazaki, R. Tetrahedron Lett. 1999, 40, 3569-3572. Boerrigter, H.; Tomasberger, T.; Verboom, W.; Reinhoudt, D. N. Eur. J. Org. Chem. 1999, 665-674. Duzamet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788.
7. Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Chem. Soc. 1999, 121, 4928-4929. Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139 and references therein.
8. Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Chem. Soc. 1999, 121, 4928-4929. Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139 and references therein.
9. Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967.
10. Chapman, R. G.; Sherman, J. C. J. Org. Chem. 1998, 63, 4103-4110 and references therein.
11. The synthesis and stability constants of complexes of one singly and two 1,2-doubly bridged biscavitands were recently reported: Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 9818-9826.
12. Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132-143. Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1727-1729.
13. Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132-143. Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1727-1729.
14. Sherman, J. C.; Knobler, C. B.; Cram; D. J. J. Am. Chem. Soc. 1991, 113, 2167-2172.
15. Cram, D. J.; Tanner, M. E.; Knobler, C. B. J. Am. Chem. Soc. 1991, 113, 7717-7727. Apparently at odds with this result, Konishi et al. reported a bromination with 2 equiv of NBS which resulted in the selective (10:1 A,C/A,B) preparation of an A,C-dibromoresorcinarene in 30% yield: Konishi, H.; Nakamaru, H.; Nakatani, H.; Ueyama, T.; Kobayashi, K.; Morikawa, O. Chem. Lett. 1997, 185-186.
16. Cram, D. J.; Tanner, M. E.; Knobler, C. B. J. Am. Chem. Soc. 1991, 113, 7717-7727. Apparently at odds with this result, Konishi et al. reported a bromination with 2 equiv of NBS which resulted in the selective (10:1 A,C/A,B) preparation of an A,C-dibromoresorcinarene in 30% yield: Konishi, H.; Nakamaru, H.; Nakatani, H.; Ueyama, T.; Kobayashi, K.; Morikawa, O. Chem. Lett. 1997, 185-186.
17. Sorrell, T. N.; Richards, J. L. Synlett 1992, 155.
18. Timmerman, P.; van Mook, M. G. A.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt; D. N. Tetrahedron Lett. 1992, 33, 3377-3380. Timmerman, P.; Boerrigter, H.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 167-191.
19. Timmerman, P.; van Mook, M. G. A.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt; D. N. Tetrahedron Lett. 1992, 33, 3377-3380. Timmerman, P.; Boerrigter, H.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 167-191.
20. Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson. J. L.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 2229-2237.
21. The solubility of lithiated cavitands is presumably much higher than the parent tetrabromocavitand 1, thereby facilitating the conversion to the tetralithiocavitand.
22. Under these conditions, a white suspension is formed immediately after addition of the n-BuLi. This suspension dissolves within a few seconds.
23. For general details, see the Supporting Information.
24. Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. Am. Chem. Soc. 1989, 111, 5397-5404.