Solvolysis-decomposition of 2-adamantyl chloroformate: Evidence for two reaction pathways

Journal of Organic Chemistry

Volumn 68, Issue 9, 2003, Pages 3425-3432

  Kyong, Jin Burm ^a   Yoo, Jung Suk ^a   Kevill, Dennis N ^b  

^a Hanyang University   (South Korea)

^b NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; ESTERS; ETHANOL; ETHERS;

SOLVOLYTIC CONDITIONS;

DECOMPOSITION;

2 ADAMANTYL CHLOROFORMATE; ALCOHOL; CHLORIDE; ETHER; FORMIC ACID DERIVATIVE; METHANOL; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DECOMPOSITION; REACTION ANALYSIS; SOLVOLYSIS;

EID: 0037414520     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0207426     Document Type: Article

References (41)

1. Kevill, D. N.; Kim, J. C.; Kyong, J. B. J. Chem. Res., Synop. 1999, 150.
2. Kevill, D. N.; D'Souza, M. J. J. Org. Chem. 1998, 63, 2120.
3. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 2002, 240.
4. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1997, 1721.
5. Kyong, J. B.; Park, B.-C.; Kim, C.-B.; Kevill, D. N. J. Org. Chem. 2000, 65, 8051.
6. Kyong, J. B.; Kim, Y.-G.; Kim, D. K.; Kevill, D. N. Bull. Korean Chem. Soc. 2000, 21, 662.
7. (a) Kevill, D. N.; Weitl, F. L. Tetrahedron Lett. 1971, 707.
8. (b) Kevill, D. N.; Kyong, J. B.; Weitl, F. L. J. Org. Chem. 1990, 55, 4304.
9. Kevill, D. N.; Kyong, J. B. J. Org. Chem. 1992, 57, 258.
10. Shorter, J. Correlation Analysis of Organic Reactivity; Research Studies Press: New York, 1982; pp 54-59.
11. Winstein, S.; Grunwald, E.; Jones, H. W. J. Am. Chem. Soc. 1951, 73, 2700.
12. Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845.
13. Kevill, D. N. In Advances in Quantitative Structure-Property Relationships; Charton, M., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 1, pp 81-115.
14. Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121.
15. (a) Bentley, T. W.; Carter, G. E. J. Am. Chem. Soc. 1982, 104, 5741.
16. (b) Kevill, D. N.; D'Souza, M. J. J. Chem. Res., Synop. 1993, 174.
17. (c) Lomas, J. S.; D'Souza, M. J.; Kevill, D. N. J. Am. Chem. Soc. 1995, 117, 5891.
18. Shiner, V. J., Jr.; Fisher, R. D. J. Am. Chem. Soc. 1971, 93, 2553.
19. Burfield, D. R.; Smithers, R. H. J. Org. Chem. 1983, 48, 2420.
20. Faurholt, C.; Gjaldbaek, J. C. Dansk Tids. Farm. 1945, 19, 255; Chem. Abstr. 1946, 40, 513.
21. Faurholt, C.; Gjaldbaek, J. C. Dansk Tids. Farm. 1945, 19, 255; Chem. Abstr. 1946, 40, 513.
22. Koo, I. S.; Yang, K.; Kang, K.; Lee, I.; Bentley, T. W. J. Chem. Soc., Perkin Trans. 2 1998, 1179.
23. Bentley, T. W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1976, 98, 7658.
24. Schadt, F. L.; Bentley, T. W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1976, 98, 7667.
25. Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1.
26. Fort, R. C., Jr.; Schleyer, P. v. R. Chem. Rev. 1964, 64, 277.
27. Kevill, D. N.; Kolwyck, K. C.; Shold, D. M.; Kim, C.-B. J. Am. Chem. Soc. 1973, 95, 6022.
28. Kevill, D. N.; Bond, M. W.; D'Souza, M. J. J. Org. Chem. 1997, 62, 7869.
29. Kevill, D. N.; D'Souza, M. J. Can. J. Chem. 1999, 77, 1118.
30. Bentley, T. W.; Roberts, K. J. Chem. Soc., Perkin Trans. 2 1989, 1055.
31. D'Souza, M. J.; Kevill, D. N.; Bentley, T. W.; Devaney, A. C. J. Org. Chem. 1995, 60, 1632.
32. Kevill, D. N.; D'Souza, M. J. J. Chem. Res., Synop. 1994, 190.
33. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, 1987; p 341.
34. McManus, S. P.; Sedaghat-Herati, M. R.; Karaman, R. M.; Neamati-Mazraek, N.; Cowell, S. M.; Harris, J. M. J. Org. Chem. 1989, 54, 1911.
35. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
36. Moss, R. A.; Johnson, L. A.; Yan, S.; Toscano, J. P.; Showalter, B. M. J. Am. Chem. Soc. 2000, 122, 11256 and references therein.
37. Moss, R. A.; Zheng, F.; Fedé, J.-M.; Ma, Y.; Sauers, R. R.; Toscano, J. P.; Showalter, B. M. J. Am. Chem. Soc. 2002, 124, 5258.
38. Moss, R. A.; Zheng, F.; Fedé, J.-M.; Sauers, R. R. Org. Lett. 2002, 4, 2341.
39. Bentley, T. W.; Carter, G. E. J. Org. Chem. 1983, 48, 579.
40. Van Zorge, J. A.; Strating, J.; Wyberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
41. Allard, B.; Casadevall, A.; Casadevall, E.; Largeau, C. Nouv. J. Chim. 1980, 4, 539.