Remarkable Alkali Cation Template Effect in 1,5-Bridged Calix[8]arenes

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1605-1608

  Consoli, Grazia M L ^a   Cunsolo, Francesca ^a   Geraci, Corrada ^a   Neri, Placido ^b  

^a CNR   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001184987     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015766y     Document Type: Article

References (32)

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2. Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. Templated Organic Synthesis; Diederich, F., Stang, P. J.; Eds.; Wiley-VCH: Weinheim, 1999.
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8. Kidd, T. J.; Leigh, D. A.; Wilson, A. J. J. Am. Chem. Soc. 1999, 121, 1599.
9. It has been demonstrated that even less specific host-guest interactions strongly affect the formation of carcerand structures: Makeiff, D. A.; Pope, D. J.; Sherman, J. C. J. Am. Chem. Soc. 2000, 122, 1337.
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11. Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 41, 10002. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. It has been proved that template effect can influence product distribution in a dynamic combinatorial library: Cousins, G. R. L.; Furlan, R. L. E.; Ng, Y.-F.; Redman, J. E.; Sanders, J. K. M. Angew. Chem., Int. Ed. 2001, 40, 423.
12. Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 41, 10002. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. It has been proved that template effect can influence product distribution in a dynamic combinatorial library: Cousins, G. R. L.; Furlan, R. L. E.; Ng, Y.-F.; Redman, J. E.; Sanders, J. K. M. Angew. Chem., Int. Ed. 2001, 40, 423.
13. For comprehensive reviews on calixarenes see: Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001.
14. For comprehensive reviews on calixarenes see: Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001.
15. For comprehensive reviews on calixarenes see: Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998. Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001.
16. Shinkai, S. Tetrahedron 1993, 49, 8933. Yamamoto, H.; Sakaki, T.; Shinkai, S. Chem. Lett. 1994, 469.
17. Shinkai, S. Tetrahedron 1993, 49, 8933. Yamamoto, H.; Sakaki, T.; Shinkai, S. Chem. Lett. 1994, 469.
18. For example, the conformers distribution of mobile tetramethoxycalix[4]arenes is influenced by the nature of metal cation (Iwamoto, K.; Ikeda, A.; Araki, K.; Harada, T.; Shinkai, S. Tetrahedron 1993, 49, 609), as well as by nitric oxide guest (Rathore, R.; Lindeman, S. V.; Rao, K. S. S. P.; Sun, D.; Kochi, J. K. Angew. Chem., Int. Ed. 2000, 39, 2123).
19. For example, the conformers distribution of mobile tetramethoxycalix[4]arenes is influenced by the nature of metal cation (Iwamoto, K.; Ikeda, A.; Araki, K.; Harada, T.; Shinkai, S. Tetrahedron 1993, 49, 609), as well as by nitric oxide guest (Rathore, R.; Lindeman, S. V.; Rao, K. S. S. P.; Sun, D.; Kochi, J. K. Angew. Chem., Int. Ed. 2000, 39, 2123).
20. For a review see: Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713.
21. Otsuka, H.; Araki, K.; Shinkai, S. Tetrahedron 1995, 51, 8757. Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457.
22. Otsuka, H.; Araki, K.; Shinkai, S. Tetrahedron 1995, 51, 8757. Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457.
23. 60-fullerene complexation: Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. Chem. Commun. 1996, 2615. It is also known that in lanthanide-calix[8]arene complexes the macrocycle adopts a well-defined solution conformation imposed by the strong coordination geometry of the metal centers: Bunzli, J.; Harrowfield, J. Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991; pp 211-231.
24. 60-fullerene complexation: Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. Chem. Commun. 1996, 2615. It is also known that in lanthanide-calix[8]arene complexes the macrocycle adopts a well-defined solution conformation imposed by the strong coordination geometry of the metal centers: Bunzli, J.; Harrowfield, J. Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991; pp 211-231.
25. Geraci, C.; Chessari, G.; Piattelli, M.; Neri, P. Chem. Commun. 1997, 921. Geraci, C.; Bottino, A.; Piattelli, M.; Gavuzzo, E.; Neri, P. J. Chem. Soc., Perkin Trans. 2 2000, 185.
26. Geraci, C.; Chessari, G.; Piattelli, M.; Neri, P. Chem. Commun. 1997, 921. Geraci, C.; Bottino, A.; Piattelli, M.; Gavuzzo, E.; Neri, P. J. Chem. Soc., Perkin Trans. 2 2000, 185.
27. 2, 4 H), 6.98 (s, ArH, 2 H), 7.04-7.18 (overlapped, ArH, 12 H), 7.19 (s, ArH, 2 H).
28. For further details on a similar procedure, see: Geraci, C.; Piattelli, M.; Chessari, G.; Neri, P. J. Org. Chem. 2000, 65, 5143.
29. Ikeda, A.; Akao, K.; Harada, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 1621. Ikeda, A.; Suzuki, Y.; Akao, K.; Shinkai, S. Chem. Lett. 1996, 963.
30. Ikeda, A.; Akao, K.; Harada, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 1621. Ikeda, A.; Suzuki, Y.; Akao, K.; Shinkai, S. Chem. Lett. 1996, 963.
31. 2/MeOH.
32. The salt formation is evidenced by a large increase of solubility with respect to 2, which is scarcely soluble in common organic solvents.