Nucleophilic substitution reactions of α-chloroacetanilides with benzylamines in dimethyl sulfoxide

Organic and Biomolecular Chemistry

Volumn 1, Issue 11, 2003, Pages 1989-1994

  Lee, Ki Sun ^a   Adhikary, Keshab Kumar ^a   Lee, Hai Whang ^a   Lee, Bon Su ^a   Lee, Ikchoon ^a  

^a Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; CHARGE TRANSFER; ISOTOPES; KINETIC THEORY; SUBSTITUTION REACTIONS;

CHLOROACETANILIDES; DEUTERATED BENZYLAMINE; DIMETHYL SULFOXIDE;

CHLORINE COMPOUNDS;

EID: 0038602938     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b300477e     Document Type: Article

References (62)

1. (a) J. B. Conant and W. R. Kirner, J. Am. Chem. Soc., 1924, 46, 232
2. (b) A. Streitwieser, Jr., Solvolytic Displacement Reactions, McGraw Hill, New York, 1962
3. (c) S. D. Ross, M. Finkelstein and R. C. Petersen, J. Am. Chem. Soc., 1968, 90, 6411
4. (d) A. Halvorsen and J. Songstad, J. Chem. Soc., Chem. Commun., 1978, 327.
5. (a) F. Carrion and M. J. S. Dewar, J. Am. Chem. Soc., 1985, 106, 3531
6. (b) R. D. Back, B. A. Coddens and G. J. Wolber, J. Org. Chem. 1986, 51, 1030
7. (c) T. I. Yousaf and E. S. Lewis, J. Am. Chem. Soc. 1987, 109, 6137.
8. (a) T. K. Brunck and F. Weinhold, J. Am. Chem. Soc., 1979, 101, 1700
9. (b) A. E. Reed and L. E. Curtiss, Chem. Rev., 1988, 88, 735.
10. (a) J. W. Baker, Trans. Faraday Soc., 1951, 37, 643
11. (b) C. A. Bunton, Nucleophilic Substitution at a Saturated Carbon Atom, Elsevier, New York, 1963 p. 5
12. (c) S. Winstein, E. Grunwald and H. W. Jone, J. Am. Chem. Soc., 1951, 73, 2700.
13. (a) M. J. S. Dewar, The Electronic Theory of Organic Chemistry Oxford University Press, Oxford, 1949, p. 73
14. (b) D. J. McLennan and A. Pross, J. Chem. Soc., Perkin Trans. 2, 1984, 981.
15. H. J. Koh, K. L. Han, H. W. Lee and I. Lee, J. Org. Chem., 2000, 65, 4706.
16. (a) I. Lee, Chem. Soc. Rev., 1990, 19, 317
17. (b) I. Lee, Adv. Phys. Org. Chem., 1992, 27, 57
18. (c) I. Lee and H. W. Lee, Collect. Czech. Chem. Commun., 1999, 64, 1529.
19. C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165.
20. L. F. Blackwell, A. Fischer, J. Miller, R. D. Topsom and J. Vaughan, J. Chem. Soc., 1964, 3588.
21. I. Lee, S. W. Hong, H. J. Koh, Y. Lee, B.-S. Lee and H. W. Lee, J. Org. Chem., 2001, 66, 8549.
22. W. J. Spillane, G. Hogan, P. McGrath, J. King and C. Brack, J. Chem. Soc., Perkin Trans. 2, 1996, 2099.
23. (a) K. Fukui, Theory of Orientation and Stereoselection, Springer-Verlag, Berlin, 1975
24. (b) I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976.
25. (a) H. G. Li, C. K. Kim, B.-S. Lee, C. K. Kim, S. K. Rhee and I. Lee, J. Am. Chem. Soc., 2001, 123, 2326
26. (b) I. Lee, Int. Rev. Phys. Chem., 2003, 22, in press.
27. (a) C. K. Kim, H. G. Li, H. W. Lee, C. K. Sohn, Y. I. Chun and I. Lee, J. Phys. Chem. A, 2000, 104, 4069
28. (b) I. Lee, C. K. Kim, H. G. Li, C. K. Sohn, C. K. Kim, H. W. Lee and B.-S. Lee, J. Am. Chem. Soc., 2000, 122, 11162.
29. (a) E. A. Castro, M. J. Salas and J. G. Santos, J. Org. Chem., 1994, 59, 30
30. (b) E. A. Castro, L. Leandro, P. Millan and J. G. Santos, J. Org. Chem., 1999, 64, 1953
31. (c) E. A. Castro, P. Munoz and J. G. Santos, J. Org. Chem., 1999, 64, 8298
32. (d) H. K. Oh, S. K. Kim, I. H. Cho, H. W. Lee and I. Lee, J. Chem. Soc., Perkin Trans. 2, 2000, 2306.
33. (a) N. D. Epiotis, W. R. Cherry, S. Shaik, R. L. Yates and F. Bernardi, Structural Theory of Organic Chemistry, Springer-Verlag, Berlin, 1977
34. (b) T. A. Albright, J. K. Burdett and M. H. Whangbo, Orbital Interaction in Chemistry, Wiley, New York, 1985, chps. 2 and 3.
35. I. Lee, H. Y. Kim, H. K. Kang and H. W. Lee, J. Org. Chem., 1988, 53, 2678.
36. I. Lee, Y. H. Choi and H. W. Lee, J. Chem. Soc., Perkin Trans. 2, 1988, 1537.
37. I. Lee, W. H. Lee and H. W. Lee, J. Org. Chem., 1991, 56, 4682.
38. K. H. Yew, H. J. Koh, H. W. Lee and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1995, 2263.
39. A. K. Guha, H. W. Lee and I. Lee, J. Org. Chem., 2000, 65, 12.
40. H. J. Koh, H. C. Lee, H. W. Lee and I. Lee, Bull. Korean Chem. Soc., 1995, 16, 839.
41. T.-H. Kim, C. Huh, B.-S. Lee and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1995, 2257.
42. B. C. Lee, J. H. Yoon, C. G. Lee and I. Lee, J. Phys. Org. Chem., 1994, 7, 273.
43. H. K. Oh, C. H. Shin and I. Lee, J. Chem. Soc., Perkin Trans. 2, 1995, 1169.
44. H. J. Koh, O. S. Kim, H. W. Lee and I. Lee, J. Phys. Org. Chem., 1997, 10, 725.
45. H. J. Koh, K. L. Han, H. W. Lee and I. Lee, J. Org. Chem., 1998, 63, 9834.
46. I. Lee, Bull. Korean Chem. Soc., 1994, 15, 985.
47. I. Lee, Chem. Soc. Rev., 1995, 24, 223.
48. I. Lee, H. J. Koh, B.-S. Lee, D. S. Sohn and B. C. Lee, J. Chem. Soc., Perkin Trans. 2, 1991, 1741.
49. -1 for 5 and 6, respectively.
50. M. J. Gresser and W. P. Jencks, J. Am. Chem. Soc., 1977, 99, 6970.
51. E. A. Castro, M. Cubillos and J. G. Santos, J. Org. Chem., 1999, 64, 6342.
52. H. J. Koh, K. L. Han and I. Lee, J. Org. Chem., 1999, 64, 4783.
53. H. K. Oh, M. H. Ku, H. W. Lee and I. Lee, J. Org. Chem., 2002, 67, 8995.
54. (a) E. A. Castro and C. Ureta, J. Org. Chem., 1990, 55, 1076
55. (b) E. A. Castro, C. A. Araneda and J. G. Santos, J. Org. Chem., 1997, 62, 126
56. (c) E. A. Castro, Chem. Rev., 1999, 99, 3505.
57. (a) A. Pross, Adv. Phys. Org. Chem., 1977, 14, 69
58. (b) E. Buncel and H. Wilson, J. Chem. Educ., 1987, 64, 475.
59. (a) I. Lee, B.-S. Lee, H. J. Koh and B. D. Chang, Bull. Korean Chem. Soc., 1995, 16, 277
60. (b) H. J. Koh, I. Lee and H. W. Lee, Can. J. Chem., 1998, 76, 710.
61. (a) A. I. Vogel, Practical Organic Chemistry, 5th edn., Longmans, London, 1988, p. 918
62. (b) S.-C. Kim and B.-M. Kwon, Synthesis, 1982, 795.