Kinetics and mechanism of the pyridinolysis of phenyl chloroformates in acetonitrile

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9834-9839

  Koh, Han Joong ^a   Han, Kwang Lae ^a,b   Lee, Hai Whang ^a,c   Lee, Ikchoon ^a,c  

^a Jeonju National University of Education   (South Korea)

^b Gwangju National University of Education   (South Korea)

^c Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORMIC ACID PHENYL ESTER; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; LYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 20644453756     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9814905     Document Type: Article

References (28)

1. (a) Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1968, 90, 2622.
2. (b) Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963.
3. (c) Fersht, A. R.; Jencks, W. P. J. Am. Chem. Soc. 1970, 92, 5442.
4. (d) Bond, P. M.; Castro, E. A.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1976, 68.
5. (e) Castro, E. A.; Gil, F. J. Am. Chem. Soc. 1977, 99, 7611.
6. (f) Castro, E. A.; Freudenberg, M. J. Org. Chem. 1980, 45, 906.
7. (g) Palling, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 4869.
8. (h) Castro, E. A.; Ibanez, F.; Salas, M.; Santos, J. G.; Sepulveda, P. J. Org. Chem. 1993, 58, 459.
9. Yew, K. H.; Koh, H. J.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkins Trans. 2 1995, 2263.
10. a values used to derive this correlation were taken from Fisher, A.; Galloway, W. J.; Vaughan, J. J. Chem. Soc. 1964, 3591.
11. Charton, M. J. Am. Chem. Soc. 1964, 86, 2033.
12. Clark, J.; Perrin, D. D. Quart. Rev. Chem. Soc. 1964, 18, 295.
13. (a) Foroughifar, N.; Leffek, K. T.; Lee, Y. G. Can. J. Chem. 1992, 70, 2856.
14. (b) Spillane, W. J.; Hogan, G.; McGrath, P.; King, J.; Brack, C. J. Chem. Soc., Perkin Trans. 2 1996, 2099.
15. Lee, I.; Koh, H. J.; Lee, B. C. J. Phys. Org. Chem. 1994, 7, 50.
16. Kim, T. H., Huh, C.; Lee, B. S.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1995, 2257.
17. Ruff, F.; Csizmadia, I. G. Organic Reactions. Equilibria, Kinetics and Mechanism; Elsevier: Amsterdam, 1994; p 330.
18. Taft, R. W.; Koppel, I. A.; Topsom, R. D.; Anvia, F. J. Am. Chem. Soc. 1990, 112, 2047.
19. Hong, S. W.; Koh, H. J.; Lee, I. J. Phys. Org. Chem., in press.
20. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans 2 1995, 973.
21. Koo, I. S.; Yang, K.; Kang, D. H.; Park, H. J.; Kang, K.; Lee, I. Unpublished.
22. (a) Lee, I. Chem. Soc. Rev. 1990, 79, 317.
23. (b) Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57.
24. (a) Lee, I.; Park, Y. K.; Huh, C.; Lee, H. W. J. Phys. Org. Chem. 1994, 7, 555.
25. (b) Lee, I. Bull. Korean Chem. Soc. 1994, 15, 985.
26. (c) Oh, H K.; Shin, C. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1995, 1169.
27. (d) Oh, H. K.; Shin, C. H.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 657.
28. Guggenheim, E. A. Phil. Mag. 1926, 2, 538.