Synthesis and association behavior of butadiyne-bridged [44](2,6)pyridinophane and [46](2,6)pyridinophane derivatives

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3265-3268

  Tobe, Yoshito ^a   Nagano, Atsushi ^a   Kawabata, Kazuya ^a   Sonoda, Motohiro ^a   Naemura, Koichiro ^a  

^a OSAKA UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0000720367     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006318d     Document Type: Article

References (27)

1. For reviews: (a) Moore, J. S. Acc. Chem. Res. 1997, 30, 402.
2. (b) Haley, M. M.; Pak, J. J.; Brand S. C. Top. Curr. Chem. 1999, 201, 81.
3. (a) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019.
4. (b) Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 2655.
5. (c) Vevkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. Nature 1994, 371, 591.
6. (d) Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019.
7. (e) Shetty, A. S.; Fischer, P. R.; Stork, K. F.; Bohn, P. W.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9409.
8. (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713.
9. (b) Morrison, D. L.; Höger, S. Chem. Commun. 1996, 2313.
10. (c) Höger, S.; Meckenstock, A.-D.; Müller, S. Chem. Eur. J. 1998, 4, 2423.
11. (d) Höger, S.; Meckenstock, A.-D. Chem. Eur. J. 1999, 5, 1686.
12. (a) Tobe, Y.; Utsumi, N.; Kawabata, K.; Naemura, K. Tetrahedron Lett. 1996, 37, 9325.
13. (b) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
14. The diagonal N-N distances of 3 and 5 estimated from their AM1-optimized structures are 11 and 15 Å, respectively. The corresponding distance of 4 is 10 Å.
15. Aoki, K. Yakugaku Zasshi 1953, 73, 969.
16. For a review, see: Sonogashira, K. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 521-549.
17. Hay, A. S. J. Org. Chem. 1962, 27, 3320.
18. (a) Eglinton, G.; Galbraith, A. R. Proc. R. Chem. Soc. 1957, 350.
19. (b) Behr, O. M.; Eglinton, G.; Galbraith, A. R.; Raphael, R. A. J. Chem. Soc. 1960, 3614.
20. Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 2053.
21. The AMI calculations were performed using the SPARTAN ver. 5.0 program package; Wavefunction, Inc., Irvine, CA.
22. 3) did not give a unique solution.
23. The calculated (AM1) dipole moment of methyl 2,6-diethynylpyridine-4-carboxylate (1.26 D) is pointing from C(4) to the nitrogen atom, whereas that of methyl 3,5-diethynylbenzoate (0.85 D) is pointing to the opposite direction, i.e., to the ester group.
24. (a) Williams, J. H. Acc. Chem. Res. 1993, 26, 593.
25. (b) Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019.
26. (c) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641.
27. (d) Ponzini, F.; Zagha, R.; Hardcastle, K.; Siegel, J. S. Angew. Chem., Int. Ed. 2000, 39, 2323.