Solvation and nucleophilic reactivity of conjugate-base anions of 5-methyl Meldrum's acid and of 3,3-dimethylbarbituric acid in acetonitrile-methanol

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 6, 1999, Pages 1181-1186

  Kondo, Yasuhiko ^a   Yano, Kouji ^b   Urade, Miyuki ^a   Yamada, Aki ^a   Kouyama, Ruiko ^a   Takagi, Tatsuya ^b  

^a Osaka Prefecture University   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002646683     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900283i     Document Type: Article

References (29)

1. F. G. Bordwell, H. E. Fried, D. L. Hughes, T.-Y. Lynch, A. V. Satish and Y. E. Whang, J. Org. Chem., 1990, 55, 3330.
2. F. G. Bordwell, Acc. Chem. Res., 1988, 21, 456.
3. X.-M. Zhang and F. G. Bordwell, J. Org. Chem., 1994, 59, 6456.
4. E. M. Arnett, S. G. Maroldo, S. L. Schilling and J. A. Harrelson, J. Am. Chem. Soc., 1984, 106, 6759.
5. M. J. Bausch, C. Guadalupe-Fasano, R. Gostowski, D. Selmarten and A. Vaughn, J. Org. Chem., 1991, 56, 5640.
6. F. J. Millero, J. C. Ahluwalia and L. G. Hepler, J. Chem. Eng. Data, 1965, 10, 199.
7. M. J. Bausch, B. David, P. Dobrowolski, C. Guadalupe-Fasano, R. Gostowski, D. Selmarten, V. Prasad, A. Vaughn and L.-H. Wang, J. Org. Chem., 1991, 56, 5643.
8. J. N. Bronsted and K. J. Pedersen, Z. Phys. Chem., 1924, 108, 185.
9. C. G. Swain and C. B. Scott, J. Am. Chem. Soc., 1953, 75, 141.
10. J. O. Edwards and R. G. Pearson, J. Am. Chem. Soc., 1962, 84, 16.
11. C. D. Ritchie, Can. J. Chem., 1986, 64, 2239.
12. E. S. Lewis, T. A. Douglas and M. L. McLaughlin, in Nucleophilicity, eds. J. M. Harris and S. P. McManus, Advances in Chemistry Series, No. 215, American Chemical Society, Washington DC, 1987, ch. 3 and references cited therein.
13. Y. Kondo, T. Tsukamoto and C. Moriguchi, J. Chem. Soc., Perkin Trans. 2, 1996, 1699.
14. Y. Kondo, T. Tsukamoto and N. Kimura, J. Chem. Soc., Perkin Trans. 2, 1997, 1765.
15. Y. Kondo, M. Ittoh and S. Kusabayashi, J. Chem. Soc., Faraday Trans., 1982, 78, 2793.
16. Y. Kondo, T. Fujiwara, A. Hayashi and S. Kusabayashi, J. Chem. Soc., Faraday Trans., 1989, 85, 2931.
17. Y. Kondo, T. Fujiwara, A. Hayashi, S. Kusabayashi and T. Takagi, J. Chem. Soc., Perkin Trans. 2., 1990, 741.
18. The value was calculated from the data given in ref. 20 and 21.
19. The value was calculated from the data given in ref. 17 and 22.
20. J. W. Larson and L. G. Hepler, in Solute-Solvent Interactions, ed. J. F. Coetzee and C. D. Ritchie, Marcell Dekker, New York, 1969, vol. 1, ch. 2.
21. Y. Kondo, K. Kondo and S. Kusabayashi, J. Chem. Soc., Perkin Trans. 2, 1993, 1141.
22. Y. Kondo, O. Nonaka, K. Iwasaki, T. Kuwamoto and T. Takagi, J. Chem. Soc., Perkin Trans. 2, 1994, 473.
23. Y. Kondo, W. Sugitani, M. Tokui and T. Takagi, J. Chem. Soc., Perkin Trans. 2, 1995, 1049.
24. J. F. J. Dippy and S. R. C. Hughes, Tetrahedron, 1963, 19, 1527.
25. I. Koppel, J. Koppel, I. Leito, V. Pihl, L. Grehn and U. Ragnarsson, J. Chem. Res. (S), 1994, 212.
26. E. M. Arnett, S. Venimadhavan and K. Amarnath, J. Am. Chem. Soc., 1992, 114, 5598.
27. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209. MOPAC93 program package, Dr J. J. P. Stewart and Fujitsu Ltd., Tokyo, Japan.
28. Y. Kondo, O. Nonaka, K. Iwasaki, T. Kuwamoto and T. Takagi, J. Chem. Soc., Faraday Trans., 1994, 90, 121.
29. Y. Kondo, S. Kusabayashi and T. Mitsuhashi, J. Chem. Soc., Perkin Trans. 2, 1988, 1799.