Hydrophobic Effects in 1,3-Dipolar Cycloaddition of C,N-Diphenylnitrone with Dibutyl fumarate in Aqueous Solutions

Abstract

The reaction rate of 1,3-dipolar cycloaddition of C,N-diphenylnitrone with dibutylfumarate increases dramatically in aqueous solutions relative to other solvents.

References

1. C.-J. Li, Chem. Rev., 1993, 93, 2023.
2. J. J. Gajewski, Acc. Chem. Res., 1997, 30, 219.
3. C. Cativiela, J. J. Garcia, R. M. Martinez, J. A. Mayoral and L. Salvatella, J. Chem. Soc., Perkin Trans 2, 1997, 653.
4. J. W. Wijnen, S. Zavarise and J. B. F. N. Engberts, J. Org. Chem., 1996, 61, 2001.
5. J. W. Wijnen and J. B. F. N. Engberts, J. Org. Chem., 1997, 62, 2039.
6. C. K. Pai and M. B. Smith, J. Org. Chem., 1995, 60, 3731.
7. S. Otto, W. Blokzijl and J. B. F. N. Engberts, J. Org. Chem., 1994, 59, 5372.
8. Y. Inoue, K. Araki and S. Shiraishi, Bull. Chem. Soc. Jpn., 1991, 64, 3079.
9. J. W. Wijnen, R. A. Steiner and J. B. F. N. Engberts, Tetrahedron Lett., 1995, 36, 5389.
10. J. Thomas and D. F. Evans, J. Phys. Chem., 1970, 74, 3812.
11. R. Breslow and T. Guo, J. Am. Chem. Soc., 1988, 110, 5613.
12. J. W. Wijnen et al., J. Org. Chem., 1996, 61, 9001.
13. Vogel's Textbook of Practical Organic Chemistry, 4th edn., 1978, p. 508.
14. M. Joula, D. Gree and J. Hamelin, Tetrahedron, 1973, 29, 2315.
15. O. H. Wheeler and P. H. Gore, J. Am. Chem. Soc., 1956, 78, 3363.
16. T.-R. Kim and K.-Il. Lee, Bull. Korean. Chem. Soc., 1991, 3, 273.