Transition-State Variation in the Solvolyses of para-Substiuted Phenyl Chloroformates in Alcohol-Water Mixtures

Bulletin of the Korean Chemical Society

Volumn 19, Issue 9, 1998, Pages 968-973

  Koo, In Sun ^a   Yang, Kiyull ^a   Kang, Keumduck ^a   Lee, Ikchoon ^b  

^a Gyeongsang National University   (South Korea)

^b Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001135948     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (58)

1. (a) Bender, M. L. Chem. Rev. 1960, 60, 53.
2. (b) The Chemistry of the Carbonyl Group, ed. Patai, S. Interscience, New York, 1966; 1970; Vol. 1-2.
3. (c) Jencks, W. P. Catalysis in Chemistry and Enzymology, McGraw-Hill: New York, 1968.
4. (d) Jencks, W. P. Acc. Chem. Res. 1980, 13, 161.
5. (e) Guthrie, J. P. Acc. Chem. Res. 1983, 16, 22.
6. (f) Baer, S.; Brinkman, E. A.; Brauman, J. I. J. Am. Chem. Soc. 1991, 113, 805.
7. (g) Williams, A. Chem. Soc. Rev. 1994, 23, 93.
8. (a) Yamabe, S.; Minato, S. J. Org. Chem. 1983, 48, 2972.
9. (b) Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1987, 109, 3856.
10. (c) Madura, J. D.; Jorgensen, W. L. J. Am. Chem. Soc. 1986, 108, 2517.
11. (d) Park, Y. S.; Kim, C. K.; Lee, B. S.; Lee, I.; Lim, W. M.; Kim, W. K. J. Phys. Org. Chem. 1995, 8, 35.
12. (a) Bentley, T. W.; Jones, R. O. J. Chem. Soc., Perkin Trans. 2 1993, 2351.
13. (b) Song, B. D.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 8470.
14. (c) Kivinen, A. The Chemistry of Acyl Halides, Patai, S., Ed; Wiley: New York, 1972.
15. (d) Queen, A. Can. J. Chem. 1967, 45, 1619.
16. (a) Bentley, T. W.; Shim, C. S. J. Chem. Soc., Perkin Trans. 2, 1993, 1659.
17. (b) Bentley, T. W.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1989, 1385.
18. Jedrzejczak, M.; Motie, R. E.; Satchell, D. P. N.; Satchell, R. S.; Wassef, W. N. J. Chem. Soc., Perkin Trans. 2 1994, 1471.
19. (a) Shpanko, I. V.; Titsku, G. D.; Litvinenko, L. M.; Eremeev, M. A. Reakts. Sposobon. Org. Soedin. 1973, 10, 187.
20. (b) Litvinenko, L. M.; Shpanko, I. V.; Korostylev, A. P. Zh. Org. Khim. 1981, 17, 972.
21. (c) Shpanko, I. V. Mendeleev Commun. 1991, 119.
22. Rogne, O. J. Chem. Soc., Perkin Trans. 2 1975, 1486.
23. (a) Lee, I.; Shim, C. S.; Chung, S. Y.; Kim, H. Y.; Lee, H. W. J. Chem. Soc., Perkin Trans. 2 1988, 1919.
24. (b) Lee, I.; Koh, H. J.; Lee, B. C. J. Phys. Org. Chem. 1994, 7, 50.
25. Song, B. D.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 8479.
26. Oh, J.; Yang, K.; Koo, I. S.; Lee, I. J. Chem. Res. 1993, 310.
27. Jedrzejczak, M.; Moite, R. E.; Satchell, D. P. N. J. Chem. Soc., Perkin Trans. 2 1993, 599.
28. Bentley, T. W.; Jones, R. O.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1994, 753.
29. Exner, O. J. Chem. Soc., Perkin Trans. 2 1993, 973.
30. (a) Bentley, T. W.; Carter, G. E.; Harris, H. C. J. Chem. Soc., Perkin Trans. 2 1985, 938.
31. (b) Bentley, T. W.; Harris, H. C. J. Chem. Soc., Perkin Trans. 2 1986, 619.
32. (c) Bentley, T. W.; Koo, I. S. J. Chem. Soc., Chem. Commun. 1988, 41.
33. Ta-Shma, R.; Rappoport, Z. Adv. Phys. Org. Chem. 1992, 27, 239.
34. (a) Bentley, T. W.; Jones, R. O. J. Chem. Soc., Perkin Trans. 2 1992, 743.
35. (b) Jones, R. O. M. Phil. Thesis, University of Wales, 1991.
36. Bentley, T. W.; Ryu, Z. H. J. Chem. Soc., Perkin Trans. 2 1994, 761.
37. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1981, 103, 3702.
38. Lee, I.; Song, C. H. Bull. Korean Chem. Soc. 1986, 7, 186.
39. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1997, 1721.
40. Bentley, T. W.; Harris, H. C. J. Org. Chem. 1988, 53, 724.
41. Koo, I. S.; Bentley, T. W.; Kang, D. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1991, 175.
42. Lee, I.; Koo, I. S. Tetrahedron 1983, 39, 1803.
43. Bentley, T. W.; Llewellynm, G. Adv. Phys. Org. Chem. 1990, 17, 121.
44. Koo, I. S.; Lee, I.; Oh, J.; Yang, K.; Bentley, T. W. J. Phy. Org. Chem. 1993, 6, 223.
45. (a) Koo, I. S.; Yang, K.; Kang, K.; Park, J. K.; Oh, H. K.; Lee, I. Bull. Korean Chem. Soc. 1997, 18, 179.
46. (b) Koo, I. S.; Yang, K.; Kang, K.; Koo, J. C.; Park, J. K.; Lee, I. Bull. Korean Chem. Soc. 1997, 18, 1017.
47. Koo, I. S.; Yang, K.; Kang, K.; Lee, I.; Bentley, T. W. J. Chem. Soc., Perkin Trans. 2 1998, in press.
48. Lee, I.; Koo, I. S.; Shon, S. C.; Lee, H. W. Bull. Korean Chem. Soc. 1982, 3, 92.
49. Johnson, C. D. The Hammett Equation; Cambrige Univ. Press: Cambrige, 1973, Chap. 1.
50. (a) Oh, H. K.; Kwon, Y. B.; Cho, I. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1994, 1697.
51. (b) Oh, H. K.; Kwon, Y. B.; Chung, D. S.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 827.
52. (c) Lee, I. Chem. Soc. Rev. 1995, 24, 223.
53. (a) Murrell, J. M.; Randic, M.; Williams, D. J. Proc. Roy. Soc. 1965, A284, 566.
54. (b) Fueno, T.; Nagase, S.; Tatsumi, K.; Yamaguchi, K. Theoret. Chim. Acta 1972, 26, 48.
55. (c) Fukui, K.; Fujimoto, H. Bull. Chem. Soc. Jpn. 1968, 41, 1989.
56. (d) Morokuma, K. J. Chem. Phys. 1971, 55, 1236.
57. (e) Kollman, P. A. Acc. Chem. Res. 1977, 10, 365.
58. (f) Lee, I. Prog. Chem. and Chem. Industry 1977, 17, 383.