Kinetics and mechanism of aminolysis of phenyl acetates and phenyl trimethylacetates in dimethyl sulfoxide

Journal of the Chemical Society. Perkin Transactions 2

Volumn 7, Issue , 1996, Pages 1353-1357

  Koh, Han Joong ^a   Kim, Seung Il ^a   Lee, Byung Choon ^b   Lee, Ikchoon ^a  

^a Inha University   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001504826     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29960001353     Document Type: Article

References (35)

1. (a) M. L. Bender, Chem. Rev., 1960, 60, 53;
2. (b) W. P. Jencks and M. Gilchrist, J. Am. Chem. Soc., 1968, 90, 2622;
3. (c) E. A. Castro and C. L. Santander, J. Org. Chem., 1985, 50, 3595;
4. (d) P. M. Bond, E. A. Castro and R. B. Moodie, J. Chem. Soc., Perkin Trans. 2, 1976, 68;
5. (e) E. A. Castro and M. Freudenberg, J. Org. Chem., 1980, 45, 906;
6. (f) E. A. Castro and C. Ureta, J. Org. Chem., 1990, 55, 1676;
7. (g) E. A. Castro, F. Ibanez, A. M. Saitua and J. G. Santos, J. Chem. Res., 1993, (S) 56, (M) 0317-0327;
8. (h) M. J. Gresser and W. P. Jencks, J. Am. Chem. Soc., 1977, 99, 6963;
9. (i) D. J. Hupe and W. P. Jencks, J. Am. Chem. Soc., 1977, 99, 453.
10. A. Williams, Chem. Soc. Rev., 1994, 23, 93.
11. (a) E. A. Castro, M. T. Borquez and P. M. Parada, J. Org. Chem., 1986, 51, 5072;
12. (i) C. Castro and E. A. Castro, J. Org. Chem., 1981, 46, 2939.
13. D. J. Palling and W. P. Jencks, J. Am. Chem. Soc., 1984, 106, 4869.
14. W. P. Jencks, S. R. Brant, J. R. Gandler, G. Fendrich and C. Nakamura, J. Am. Chem. Soc., 1982, 104, 7045.
15. D. Stefanidis, S. Cho, S. Dhe-Paganon and W. P. Jencks, J. Am. Chem. Soc., 1993, 115, 1650.
16. M. J. Gresser and W. P. Jencks, J. Am. Chem. Soc., 1977, 99, 6970.
17. (a) I. Lee, Chem. Soc. Rev., 1990, 19, 317;
18. (b) I. Lee, Adv. Phys. Org. Chem., 1992, 27, 57;
19. (c) I. Lee, Chem. Soc. Rev., 1995, 24, 223;
20. (d) I. Lee, J. Phys. Org. Chem., 1992, 5, 736.
21. (a) F. M. Menger and J. H. Smith, J. Am. Chem. Soc., 1972, 94, 3824;
22. (b) M. Jedrzejczak, R. E. Motie, D. P. N. Satchell, R. S. Satchell and W. N. Wassef, J. Chem. Soc., Perkin Trans. 2, 1994, 1471.
23. (a) T. H. Kim, C. Huh, B.-S. Lee and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1995, 2257;
24. (b) H. K. Oh, C. H. Shin and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1995, 1169;
25. (c) H. J. Koh, H. C. Lee, H. W. Lee and I. Lee, Bull. Korean Chem. Soc., 1995, 16, 839.
26. (a) I. Lee, H. Y. Kim, H. K. Kang and H. W. Lee, J. Org. Chem., 1988, 53, 2678;
27. (b) I. Lee, C. S. Shim, H. W. Lee and B.-S. Lee, Bull. Korean Chem. Soc., 1991, 12, 255;
28. (c) I. Lee, H. J. Koh and H. W. Lee, J. Chem. Res., 1990, (S) 282, (M) 2177-2194.
29. I. Lee, D. Lee and C. K. Kim, submitted for publication.
30. B. D. Song and W. P. Jencks, J. Am. Chem. Soc., 1989, 111, 8479.
31. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry VCH, Weinheim, 1988, p. 218.
32. (a) R. L. Van Etten, J. F. Sebastian, G. A. Clowes and M. L. Bender, J. Am. Chem. Soc., 1967, 89, 3242;
33. (b) T. Nishioka, T. Fugita, K. Kitamura and M. Nakajima, J. Org. Chem., 1975, 40, 2520;
34. (c) J. C. Hogan and R. D. Gandour, J. Org. Chem., 1991, 56, 2821.
35. E. A. Guggenheim, Phil. Magn., 1926, 2, 538.