A kinetic study of the solvolyses of methyl and ethyl chloroglyoxalates

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 9032-9035

  Kevill, Dennis N ^a   Park, Byoung Chun ^a   Kyong, Jin Burm ^b  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

^b Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; DISSOCIATION; RATE CONSTANTS; REACTION KINETICS;

CHLOROFORMATES; ETHYL CHLOROGLYOXYLATES; GRUNWALD-WINSTEIN EQUATION; SOLVOLYSES;

ORGANIC SOLVENTS;

ETHYL CHLOROGLYOXALATE; GLYOXYLIC ACID DERIVATIVE; METHYL CHLOROGLYOXALATE; SOLVENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION KINETICS; DISSOCIATION; ELIMINATION REACTION; REACTION TIME; SOLVOLYSIS;

EID: 27444432020     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050998m     Document Type: Article

References (43)

1. For a review of early work, see: Kevill, D. N. In The Chemistry of the Functional Groups: The Chemistry of Acyl Halides; Patai, S., Ed.; Wiley-Interscience: New York, 1972; Chapter 12.
2. Koo, I. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc. 1998, 19, 968.
3. Kyong, J. B.; Park, B.-C.; Kim, C.-B.; Kevill, D. N. J. Org. Chem. 2000, 65, 8051.
4. Kevill, D. N.; Kyong, J. B.; Weitl, F. L. J. Org. Chem. 1990, 55, 4304.
5. (a) Ostrogovich, G.; Csunderlik, C.; Bacaloglu, R. J. Prakt. Chem. 1975, 317, 62.
6. (b) Csunderlik, C.; Bacaloglu, R.; Ostrogovich, G. J. Prakt. Chem. 1975, 317, 73.
7. (c) Queen, A.; Matts, T. C. Tetrahedron Lett. 1975, 1303.
8. (d) Queen, A.; McKinnon, D. M.; Bell, A. W. Can. J. Chem. 1976, 54, 1906.
9. (e) Kevill, D. N.; Bond, M. W.; D'Souza, M. J. J. Org. Chem. 1997, 62, 7869.
10. (f) Kevill, D. N.; D'Souza, M. J. Can. J. Chem. 1999, 77, 1118.
11. (g) An, S. K.; Yang, J. S.; Cho, J. M.; Yang, K.; Lee, J. P.; Bentley, T. W.; Lee, I.; Koo, I. S. Bull. Korean Chem. Soc. 2002, 23, 1445.
12. (a) Queen, A.; Nour, T. A. J. Chem. Soc., Perkin Trans. 2 1975, 935.
13. (b) Orlov, S. I.; Chimishkyan, A. L.; Grabarnik, M. S. J. Org. Chem. USSR (Engl. Transl.) 1983, 19, 1981.
14. (c) Kevill, D. N.; Kyong, J. B. J. Org. Chem. 1992, 57, 258.
15. (d) Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 2002, 240.
16. (a) Kevill, D. N.; D'Souza, M. J. J. Org. Chem. 1998, 63, 2120.
17. (b) Kyong, J. B.; Won, H.; Kevill, D. N. Int. J. Mol. Sci. 2005, 6, 87.
18. Kevill, D. N.; Kim, J. C.; Kyong, J. B. J. Chem. Res., Synop. 1999, 150.
19. Kyong, J. B.; Kim, Y.-G.; Kim, D. K.; Kevill, D. N. Bull. Korean Chem. Soc. 2000, 21, 662.
20. Kivinen, A. In The Chemistry of the Functional Groups: The Chemistry of Acyl Halides; Patai, S., Ed.; Wiley-Interscience: New York, 1972; Chapter 6.
21. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1997, 1721.
22. Faurholt, C.; Gjaldbaek, J. C. Dan. Tidsskr. Farm. 1945, 19, 255;
23. Chem. Abstr. 1946, 40, 513.
24. Stollé, R. Chem. Ber. 1914, 47, 1130.
25. (a) Simon, M. S.; Seyferth, H. McC. J. Org. Chem. 1958, 23, 1078.
26. (b) Kevill, D. N.; Weitl, F. L. J. Chem. Soc., Perkin Trans, 1 1972, 2162.
27. Cordova, T.; Rotinov, A.; Chuchani, G. J. Phys. Org. Chem. 2004, 17, 148.
28. Rhoads, S. J.; Michel, R. E. J. Am. Chem. Soc. 1963, 85, 585.
29. Kevill, D. N.; Kim, C.-B. J. Chem. Soc., Perkin Trans. 2 1988, 1353.
30. For a discussion of this treatment, see: Kevill, D. N. In Advances in Quantitative Structure-Property Relationships; Charton, M., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 1, pp 81-115.
31. Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845.
32. Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121.
33. (a) Bentley, T. W.; Carter, G. E. J. Am. Chem. Soc. 1982, 104, 5741.
34. (b) Kevill, D. N.; D'Souza, M. J. J. Chem. Res., Synop. 1993, 174.
35. Koo, I. S.; Bentley, T. W.; Kang, D. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1991, 296.
36. Leimu, R. Chem. Ber. 1937, 70, 1040.
37. Kivinen, A. Acta Chem. Scand. 1965, 19, 845.
38. Euranto, E. K.; Leimu, R. S. Acta Chem. Scand. 1966, 20, 2028.
39. Winstein, S.; Grunwald, E.; Jones, H. W. J. Am. Chem. Soc. 1951, 73, 2700.
40. Grunwald, E.; Winstein, S. J. Am. Chem. Soc. 1948, 70, 846.
41. Kevill, D. N.; Abduljaber, M. H. Croat. Chim. Acta 1992, 65, 539.
42. Pasto, D. J.; Garves, K.; Serve, M. P. J. Org. Chem. 1967, 32, 774.
43. Kevill, D. N.; Kim, C.-B. J. Org. Chem. 2005, 70, 1490.