Effective coordination of electron-donating sidearms of double-armed 15-crown-5 ethers toward alkali metal cations

Chemistry Letters

Volumn , Issue 4, 1999, Pages 283-284

  Muraoka, Masahiro ^a   Kajiya, Hiroyuki ^a   Zhang, Wanbin ^a   Kida, Toshiyuki ^a   Nakatsuji, Yohji ^a   Ikeda, Isao ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033245691     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.283     Document Type: Article

References (21)

1. a) G. W. Gokel and J. E. Trafton in "Cation Binding by Macrocycles," ed by Y. Inoue and G. W. Gokel, Marcel Dekker, Inc., New York (1990), p. 253.
2. b) G. W. Gokel and O. F. Schall in "Comprehensive Supramolecular Chemistry," ed by G. W. Gokel, Elsevier Science, Oxford (1996), Vol. 1, p. 97.
3. a) V. J. Gatto and G. W. Gokel, J.Am. Chem. Soc., 106, 8240 (1984).
4. b) A. R. Katritzky, O. V. Denisko, S. A. Belyakov, O. F. Schall, and G. W. Gokel, J. Org. Chem., 61, 7578 (1996).
5. c) X. X. Zhang, A. V. Bordunov, J. S. Bradshaw, N. K. Dally, X. Kou, and R. M. Izatt, J. Am. Chem. Soc., 117, 11507 (1995).
6. d) A. V. Bordunov, J. S. Bradshaw, X. X. Zhang, N. K. Dally, X. Kou, and R. M. Izatt, Inorg. Chem., 35, 7229 (1996).
7. Y. Nakatsuji, T. Mori, and M. Okahara, Tetrahedron Lett., 25, 2171 (1984).
8. Y. Nakatsuji, T. Nakamura, M. Yonetani, H. Yuya, and M. Okahara, J. Am. Chem. Soc., 110, 531 (1988).
9. a) E. Weber and F. Vögue, Top. Curr. Chem., 98, 1 (1981).
10. b) R. Wakita, M. Miyakoshi, Y. Nakatsuji, and M. Okahara, J. Incl. Phenom. Mol. Recogn. Chem., 10, 127 (1991).
11. c) M. Sugimoto, K. Fujiwara, R. Wakita, T. Kida, A. Masuyama, Y. Nakatsuji, and M. Okahara, Supramol. Chem., 2, 145 (1993).
12. 33) δ 1.46 (s, 6H), 3.59-3.90 (m, 16H), 4.11 (d, 2H, J=9.4 Hz), 4.37 (d, 2H, J=9.4 Hz), 7.17 (dd, 2H, J=7.3, 1.5 Hz), 7.38 (dd, 2H, J=8.1, 1.5Hz), 7.40 (dd, 2H, J=8.4, 4.0Hz), 7.44 (dd, 2H, J=8.1, 7.3Hz), 8.11 (dd, 2H, J=8.4, 1.8 Hz), 8.91 (dd, 2H, J=4.0, 1.8 Hz).
13. a) K. H. Wong, M. Bourgoin, and J. Smid, J. Chem. Soc., Chem. Commun., 1974, 715.
14. b) M. Bourgoin, K. H. Wong, J. Y. Hui, and J. Smid, J. Am. Chem. Soc., 97, 3462 (1975).
15. K. Kita, T. Kida, Y. Nakatsuji, and I. Ikeda, J. Org. Chem., 62, 8076 (1997).
16. a) T. J. Batlerham, "NMR Spectra of Simple Heterocycles, "John Wiley A Sons, New York (1973).
17. b) J. K. Sanders and B. K. Hunter, "Modern NMR Spectroscopy," Oxford University Press, Oxford (1987).
18. a) R. M. Izatt, C. Y. Zhu, N. K. Dally, J. C. Curtis, X. Kou, and J. S. Bradshaw, J. Phys. Org.Chem., 5, 656 (1992).
19. b) S. Alihodzic, M. Zinic, B. Klaic, R. Kiralj, B. Kojic-Prodic, M. Herceg, and Z. Cimerman, Tetrahedron Lett., 34, 8345 (1993).
20. For example: a) Y. Tobe, Y. Tsuchiya, H. Iketani, K. Naemura, K. Kobiro, M. Kaji, S. Tsuzuki, and K. Suzuki, J.Chem.Soc.,PerkinTrans.1, 1998, 485.
21. b) A. Merz, L. Gromann, A. Karl, L. Parkanyi, and O. Schneider, Eur. J. Org. Chem., 1998, 403.