Optimized synthesis of cavitand phenol bowls

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5846-5848

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

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DRUG SYNTHESIS; NOTE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033828563     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0004456     Document Type: Note

References (34)

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3. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
4. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
5. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
6. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
7. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
8. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
9. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
10. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
11. Recent examples: Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253-11254; Mezo, A. R.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 8983-8994; Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600-2602; Pinalli, R.; Nachtigall, F. F.; Ugozzoli, F.; Dalcanale, E. Angew. Chem., Int. Ed. 1999, 38, 2377-2380; 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; Dumazet, I.; Beer, P. D. Tetrahedron Lett. 1999, 40, 785-788. For a recent review, see Rudkevich, D. M.; Rebek, J., Jr. Eur. J. Org. Chem. 1999, 1991-2005.
12. Korner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr Chem. Eur. J. 2000, 6, 187-195; Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr J. Am. Chem. Soc. 1999, 121, 4928-4929; Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139; Chapman, R. G., Olovsson, G., Trotter, J., Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260 and references therein. A unimolecular capsule was also recently reported: Brody, M. S.; Schalley, C. A.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1640-1644.
13. Korner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr Chem. Eur. J. 2000, 6, 187-195; Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr J. Am. Chem. Soc. 1999, 121, 4928-4929; Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139; Chapman, R. G., Olovsson, G., Trotter, J., Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260 and references therein. A unimolecular capsule was also recently reported: Brody, M. S.; Schalley, C. A.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1640-1644.
14. Korner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr Chem. Eur. J. 2000, 6, 187-195; Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr J. Am. Chem. Soc. 1999, 121, 4928-4929; Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139; Chapman, R. G., Olovsson, G., Trotter, J., Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260 and references therein. A unimolecular capsule was also recently reported: Brody, M. S.; Schalley, C. A.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1640-1644.
15. Korner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr Chem. Eur. J. 2000, 6, 187-195; Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr J. Am. Chem. Soc. 1999, 121, 4928-4929; Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139; Chapman, R. G., Olovsson, G., Trotter, J., Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260 and references therein. A unimolecular capsule was also recently reported: Brody, M. S.; Schalley, C. A.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1640-1644.
16. Korner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr Chem. Eur. J. 2000, 6, 187-195; Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr J. Am. Chem. Soc. 1999, 121, 4928-4929; Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139; Chapman, R. G., Olovsson, G., Trotter, J., Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260 and references therein. A unimolecular capsule was also recently reported: Brody, M. S.; Schalley, C. A.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1640-1644.
17. Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967.
18. Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136-140; Chopra, N.; Naumann, C.; Sherman, J. C. Angew. Chem., Int. Ed. 2000, 39, 194-196; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. 1999, 38, 1955-1957; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1727-1729.
19. Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136-140; Chopra, N.; Naumann, C.; Sherman, J. C. Angew. Chem., Int. Ed. 2000, 39, 194-196; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. 1999, 38, 1955-1957; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1727-1729.
20. Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136-140; Chopra, N.; Naumann, C.; Sherman, J. C. Angew. Chem., Int. Ed. 2000, 39, 194-196; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. 1999, 38, 1955-1957; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1727-1729.
21. Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136-140; Chopra, N.; Naumann, C.; Sherman, J. C. Angew. Chem., Int. Ed. 2000, 39, 194-196; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. 1999, 38, 1955-1957; Chopra, N.; Sherman, J. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 1727-1729.
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25. Cram, D. J.; Tanner, M. E.; Knobler, C. B. J. Am. Chem. Soc. 1991, 113, 7717-7727.
26. The synthesis and stability constants of complexes of one singly-and two A, B-doubly bridged bis-cavitands were recently reported: Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 9818-9826.
27. Irwin, J. L.; Sherburn, M. S. J. Org. Chem. 2000, 65, 602-605.
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32. A significant amount of precipitation occurs in the reaction between n-BuLi and 3a/4a at [substrate] = 20 mM at -78 °C. Equilibration could be facilitated under these conditions by the forced close proximity of the lithiocavitands.
33. ie. 1a → unsymmetrical bromocavitand - unsymmetrical cavitand phenol.
34. For general details see Supporting Information.