Considerably improved grunwald-winstein correlations for solvolyses of several secondary and tertiary benzylic derivatives upon inclusion of a term governed by the aromatic ring parameter (I)

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue , 1995, Pages 973-980

  Kevill, Dennis N ^a   D’souza, Malcolm J ^b  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

^b University of Wisconsin Milwaukee at Waukesha   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049076481     PISSN: 14701820     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29950000973     Document Type: Article

References (49)

1. S. Winstein and E. Grunwald, J. Am. Chem. Soc, 1948, 70, 846.
2. S. Winstein, E. Grunwald and H. W. Jones, J. Am. Chem. Soc, 1951, 73, 2700.
3. A. H. Fainberg and S. Winstein, J. Am. Chem. Soc, 1956, 78, 2770.
4. F. L. Schadt, T. W. Bentley and P. v. R. Schleyer, J. Am. Chem. Soc, 1976,98, 7667.
5. T. W. Bentley and P. v. R. Schleyer, Adv. Phys. Org. Chem., 1977, 14, 1.
6. D. N. Kevill and G. M. L. Lin, J. Am. Chem. Soc, 1979, 101, 3916.
7. D. N. Kevill, S. W. Anderson and E. K. Fujimoto in Nucleophilicity, eds. J. M. Harris and S. P. McManus, Advances in Chemistry Series, No. 215, American Chemical Society, Washington, DC, 1987, ch. 19.
8. D. N. Kevill and S. W. Anderson, J. Org. Chem., 1991, 56, 1845.
9. A. Streitwieser., Chem. Rev., 1956, 56, 571.
10. D. J. Raber, W. C. Neal, M. D. Dukes, J. M. Harris and D. L. Mount, J. Am. Chem. Soc, 1978, 100, 8137
11. J. M. Harris, D. L. Mount, M. R. Smith, W. C. Neal, M. D. Dukes and D. J. Raber, J. Am. Chem. Soc, 1978, 100, 8147.
12. A. H. Fainberg and S. Winstein, J. Am. Chem. Soc, 1957, 79 1602-1608.
13. T. W. Bentley and G. Llewellyn, Prog. Phys. Org. Chem., 1990, 17, 121.
14. P. v. R. Schleyer and R. D. Nicholas, Am. Chem. Soc, 1961,83, 2700
15. J. L. Fry, C. J. Lancelot, L. K. M. Lam, J. M. Harris, R. C. Bingham, D. J. Raber, R. E. Hall and P. v. R. Schleyer, J. Am. Chem. Soc, 1970,92, 2538.
16. T. W. Bentley and P. v. R. Schleyer, J. Am. Chem.Soc, 1976,98,7658.
17. T. W. Bentley, C. T. Bowen, W. Parker and C. I. F. Watt, J. Am. Chem. Soc, 1979, 101,2486.
18. T. W. Bentley and G. E. Carter, J. Am. Chem. Soc, 1982, 104, 5741
19. T. W. Bentley and K. Roberts, J. Chem. Soc, Perkin Trans. 2, 1989, 1055.
20. D. N. Kevill, W. A. Kamil and S. W. Anderson, Tetrahedron Lett., 1982, 23, 4635
21. D. N. Kevill and S. W. Anderson, Am. Chem. Soc, 1986,108, 1579.
22. D. N. Kevill and M. J. D'Souza, Chem. Res. (S), 1993, 174.
23. T. W. Bentley, C. T. Bowen, D. H. Morten and P. V. R. Schleyer, J. Am. Chem. Soc, 1981,103, 5466.
24. K.-T. Liu and H.-C. Sheu, Org. Chem., 1991, 56, 3021.
25. A. H. Fainberg and S. Winstein, J. Am. Chem. Soc, 1957, 79, 1597.
26. S. Winstein, A. H. Fainberg and E. Grunwald, J. Am. Chem. Soc, 1957,79,4146.
27. T. W. Bentley, I. S. Koo and S. J. Norman, J. Org. Chem., 1991,56, 1604.
28. T. W. Bentley, J.-P. Dau-Schmidt, G. Llewellyn and H. Mayr, J. Org. Chem., 1992, 57, 2387.
29. K.-T. Liu, H.-C. Sheu, H.-I. Chen, P.-F. Chiu and C.-R. Hu, Tetrahedron Lett., 1990, 31, 3611.
30. D. N. Kevill, N. HJ Ismail and M. J. D'Souza, J. Org. Chem., 1994,59, 6303.
31. Y. Tsuji, M. Fujio and Y. Tsuno, Tetrahedron Lett., 1992, 33, 349.
32. C. A. Bunton, M. M. Mhala and J. R. Moffatt, Org. Chem., 1984, 49, 3639.
33. K.-T. Liu and H.-C. Sheu, J. Chin. Chem. Soc, 1991, 38, 29.
34. K.-T. Liu, H.-I. Chen and C.-P. Chin, Phys. Org. Chem., 1991, 4, 463.
35. K.-T. Liu, L.-W. Chang and P.-S. Chen, Org. Chem., 1992, 57, 4791.
36. K.-T. Liu, J.-S. Yang, S.-M. Chang, Y.-S. Lin, H.-C. Sheu and M.-L. Tsao, Org. Chem., 1992, 57, 3041.
37. K.-T. Liu, P.-S. Chen, P.-F. Chiu and M.-L. Tsao, Tetrahedron Lett., 1992,33, 6499.
38. K.-T. Liu, P.-S. Chen, C.-R. Hu and H.-C. Sheu, Phys. Org. Chem., 1993,6, 122.
39. K.-T. Liu and P.-S. Chen, Chem. Res. (S), 1994, 310.
40. D. N. Kevill and D. C. Hawkinson, J. Org. Chem., 1989, 54, 154.
41. B. Allard and E. Casadevall, Nouv. J. Chim., 1985, 9, 565.
42. Y. Tsuji, M. Fujio and Y. Tsuno, Bull. Chem. Soc. Jpn., 1990,63,856.
43. A. D. Allen and T. T. Tidwell, in Advances in Carbocation Chemistry, vol. 1, ed. X. Creary, Jai Press, Greenwich, Connecticut, 1989, ch. 1.
44. A. D. Allen, V. M. Kanagasabapathy and T. T. Tidwell, J. Am. Chem. Soc, 1986,108, 3470.
45. T. W. Bentley, M. Christl and S. J. Norman, J. Org. Chem., 1991,56, 6238.
46. D. N. Kevill and M. J. D'Souza, Phys. Org. Chem., 1992, 5, 287.
47. D. N. Kevill and M. J. D'Souza, J. Chem. Res. (S), 1993, 332.
48. D. N. Kevill and M. J. D'Souza, J. Phys. Org. Chem., 1993, 6, 642.
49. M. Fujio, H. Nomura, K. Nakata, Y. Saeki, M. Mishima, S. Kobayashi, T. Matsushita, K. Nishimoto and Y. Tsuno, Tetrahedron Lett., 1994, 35, 5005.