Cation binding acceleration of Diels-Alder reaction of quinocrown ethers with cyclopentadiene

New Journal of Chemistry

Volumn 22, Issue 10, 1998, Pages 1027-1029

  Tsuda, Akihiko ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008442912     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805326j     Document Type: Article

References (29)

1. (a) J.-M. Lehn, Science, 1985, 227, 849;
2. (b) Y. Inoue and T. Hakushi, J. Chem. Soc., Perkin Trans. 2, 1985, 935;
3. (c) J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1990, 29, 1304;
4. (d) V. G. Young Jr., H. L. Quiring and A. G. Sykes, J. Am. Chem. Soc., 1997, 119, 12477;
5. (e) C. Gong and H. W. Gibson, J. Am. Chem. Soc., 1997, 119, 8585;
6. (f) R. Cacciapaglia, L. Mandolini, R. Arnecke, V. Böhmer and W. Vogt, J. Chem. Soc., Perkin Trans. 2, 1998, 419.
7. Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990, ch. 13, pp. 523-547.
8. (a) V. Gold and C. M. Sghibartz, J. Chem. Soc., Chem. Commun., 1978, 507;
9. (b) D. D. S. Baker, V. Gold and C. M. Sghibartz, J. Chem. Soc., Perkin Trans. 2, 1983, 1121;
10. (c) Y. Inoue, M. Ouchi, H. Hayama and T. Hakushi, Chem. Lett., 1983, 431;
11. (d) T. Oshima and T. Nagai, J. Org. Chem., 1991, 56, 673.
12. F. Dietl, G. Gierer and A. Merz, Synthesis, 1985, 626.
13. K. Hayakawa, K. Kido and K. Kanematu, J. Chem. Soc., Perkin Trans. 1, 1988, 511.
14. (a) P. A. Grieco, J. J. Nunes and M. D. Gaul, J. Am. Chem. Soc., 1990. 112, 4595;
15. (b) H. Waldmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1306;
16. (c) D. A. Smith and K. N. Houk, Tetrahedron Lett., 1991, 32, 1549;
17. (d) M. A. Forman and W. P. Daiely, J. Am. Chem. Soc., 1991, 113, 2761;
18. (e) G. Desimoni, G. Faita, P. P. Righetti and G. Tacconi, Tetrahedron, 1991, 47, 8399;
19. (f) R. M. Pagni, G. W. Kabalka, S. Bains, M. Plesco, J. Wilson and J. Bartmess, J. Org. Chem., 1993, 58, 3130;
20. (g) P. A. Grieco and J. A. Beck, Tetrahedron Lett., 1993, 34, 7367;
21. (h) P. A. Grieco, S. T. Handy and J. A. Beck, Tetrahedron Lett., 1994, 35, 2663;
22. (i) P. A. Grieco, M. D. Kaufman, J. F. Daeuble and N. Saito, J. Am. Chem. Soc., 1996, 118, 2095.
23. R. M. Izatt and J. J. Christensene, Synthetic Multidentate Macrocyclic Compounds, Academic Press, New York, 1978, pp. 207-243.
24. (a) M. Mercer and M. R. Truter, J. Chem. Soc., Dalton Trans., 1973, 2469;
25. (b) D. L. Hughes, J. Chem. Soc., Dalton Trans., 1975, 2374.
26. A. Tsuda, T. Kawamoto and T. Oshima, Acta Crystallogr., 1998, in the press.
27. C. J. Pedersen and H. K. Frensdorff, Angew. Chem., Int. Ed. Engl., 1972, 11.
28. 3+ was calculated by MM2, MOPAC Version 94.10 in CAChe, Version 3.7, CAChe Scientific, 1994.
29. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley, London, 1976.