Hydrolysis of lipophilic esters catalyzed by a zinc(II) complex of a long alkyl-pendant macrocyclic tetraamine in micellar solution

Journal of the American Chemical Society

Volumn 118, Issue 45, 1996, Pages 10963-10970

  Kimura, Euch ^a   Hashimoto, Hiroyuki ^a   Koike, Tohru ^a  

^a HIROSHIMA UNIV SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ZINC COMPLEX;

ARTICLE; CATALYSIS; DETOXIFICATION; HYDROLYSIS; REACTION ANALYSIS;

EID: 0029860773     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961789+     Document Type: Article

References (31)

1. Review articles: (a) Kimura, E.; Koike, T. Comm. Inorg. Chem. 1991, 11, 285-301.
2. (b) Kimura, E. Tetrahedron 1992, 48, 6175-6217.
3. (c) Kimura, E. Pure Appl. Chem. 1993,65, 355-359.
4. (d) Kimura, E. Progress in Inorganic Chemistry; Karine, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491.
5. (e) Kimura, E.; Shionoya, M. Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds.; Kluwer Academic Publishers: London, 1994; pp 245-259.
6. (a) Kimura, E.; Shiota, T.; Koike, T.; Shiro, M.; Kodama, M. J. Am. Chem. Soc. 1990,112,5805-5811.
7. (b) Koike, T.; Kimura, E. J. Am. Chem. Soc. 1991, 113, 8935-8941.
8. (c) Kimura, E.; Koike, T.; Shionoya, M.; Shiro, M. Chem. Lett. 1992, 787-790.
9. (d) Koike, T.; Kimura, E.; Nakamura, I.; Hashimoto, Y.; Shiro, M. J. Am. Chem. Soc. 1992, 114, 7338-7345.
10. (e) Zhang, X.; van Eldik, R.; Koike, T.; Kimura, E. Inorg. Chem. 1993, 32, 5749-5755.
11. (f) Kimura, E.; Nakamura, I.; Koike, T.; Shionoya, M.; Kodama, Y.; Ikeda, T.; Shiro, M. J. Am. Chem. Soc. 1994, 116. 4764-4771.
12. (g) Koike, T.; Takamura, M.; Kimura, E. J. Am. Chem. Soc. 1994, 116, 8443-8449.
13. (h) Koike, T.; Kajitani, S.; Nakamura, I.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1995, 117, 1210-1219.
14. Kimura, E.; Kodama, Y.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1995, 117. 8304-8311.
15. (j) Zhang, X.; van Eldik, R. Inorg. Chem. 1995, 34, 5606-5614.
16. (a) Kaim, W.; Schwederski, B. Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life; John Wiley & Sons: New York, 1994; pp 243-266.
17. (b) Vallee, B. L.; Auld, D. S. Proc. Natl. Acd. Sei. U.SA. 1990, 57, 220-224.
18. Benning, M. M.; Kuo, J. M.; Raushel, F. M.; Holden, H. M. Biochemistry 1994, 33, 15001-15007.
19. Lai, K.; Dave, K. I.; Wild, J. R. /. Biol. Chem. 1994, 269, 16579-16584.
20. Menger, F. M.; Can, L. H.; Johnson, E.; Durst, D. H. /. Am. Cliem. Soc. 1987, 709, 2800-2803.
21. Gutsche, C. D.; Mei, G. C. J. Am. Cliem. Soc. 1985, 107, 7964-7967.
22. Tagaki, W.; Ogino, K.; Tanaka, O.; Machiya, K.; Kashihara, N.; Yoshida, T. Bull. Chem. Soc. Jpn. 1991, 64, 74-80.
23. Gellman, S. H.; Fetter, R.; Breslow, R. J. Am. Chem. Soc. 1986, 70S, 2388-2394.
24. Kimura, E.; Kuramoto, Y.; Koike, T.; Fujioka, H.; Kodama, M. J. Org. Chem. 1990, 55, 42-46.
25. Earlier, we reported that a lipophilic 14-membered macrocyclic dioxotetraamine is a selective carrier for copper(II) ion: Kimura, E.; Dalimunte, C. A.; Yamashita, A.; Machida, R. J. Chem. Soc., Chem. Commun. 1985, 1041-1043.
26. Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
27. Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem. Eur. J. 1996, 2, 617-623.
28. Bencini, A.; Bianchi, A.; Dapporto, P.; Garcia-España, E.; Micheloni, M. Inorg. Chem. 1989, 28, 1188-1191.
29. --bridged dizinc(II) complex. Norman, P. R. Inorg. Chim. Acta 1987, 130, 1-4.
30. - anion between two zinc(II) ions has no nucleophilic activity, which is somewhat similar to our dimeric complex 17: Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091-3099.
31. Martell, A. E.; Motekaitis, R. J. Determination and Use of Stability Constants, 2nd ed.; VCH: New York, 1992.