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Kinetics and Mechanism of the Aminolysis of Aryl N-Cyclohexyl Thiocarbamates in Acetonitrile

  • Jeong, Kook-Sun (Department of Chemistry and Research Institute of Physics and Chemistry, Chonbuk National University) ;
  • Oh, Hyuck-Keun (Department of Chemistry and Research Institute of Physics and Chemistry, Chonbuk National University)
  • Published : 2008.08.20
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References

  1. Koh, H. J.; Kim, O. K.; Lee, H. W.; Lee, I. J. Phys. Org. Chem. 1997, 10, 725 https://doi.org/10.1002/(SICI)1099-1395(199710)10:10<725::AID-POC943>3.0.CO;2-X
  2. Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018 https://doi.org/10.1021/ja00829a034
  3. Castro, E. A.; Ureta, C. J. Chem. Soc. Perkin Trans. 2 1991, 63
  4. Oh, H. K.; Shin, C. H.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 657
  5. Oh, H. K.; Woo, S. Y.; Shin, C. H.; Park, Y. S.; Lee, I. J. Org. Chem. 1997, 62, 5780 https://doi.org/10.1021/jo970413r
  6. Um, I.-H.; Kwon, H.-J.; Kwon, D.-S.; Park, J.-Y. J. Chem. Res. 1995, (S) 301, (M) 1801
  7. Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6970 https://doi.org/10.1021/ja00463a033
  8. Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 2001, 66, 6000 https://doi.org/10.1021/jo0100695
  9. Bond, P. M.; Moodie, R. B. J. Chem. Soc. Perkin Trans. 2 1976, 679
  10. Lee, I. Chem. Soc. Rev. 1990, 19, 317 https://doi.org/10.1039/cs9901900317
  11. Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57
  12. Lee, I.; Sung, D. D. Curr. Org. Chem. 2004, 8, 557 https://doi.org/10.2174/1385272043370753
  13. Guggenheim, E. A. Philos. Mag. 1926, 2, 538 https://doi.org/10.1080/14786442608564083
  14. Oh, H. K.; Oh, J. Y. Bull. Korean Chem. Soc. 2006, 27, 143 https://doi.org/10.5012/bkcs.2006.27.1.143
  15. Jeong, K. S.; Oh, H. K. Bull. Korean Chem. Soc. 2007, 28, 2535 https://doi.org/10.5012/bkcs.2007.28.12.2535
  16. Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 45 https://doi.org/10.1002/9780470171837.ch2
  17. Ritchie, C. D. In Solute-Solvent Interactions; Coetzee, J. F.; Ritchie, C. D., Eds.; Marcel Dekker: New York, 1969; Chapter 4
  18. Cho, B. R.; Kim, Y. K.; Maing Yoon, C. O. J. Am. Chem. Soc. 1997, 119, 691 https://doi.org/10.1021/ja961294k
  19. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2004, 69, 3150 https://doi.org/10.1021/jo049845+
  20. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165 https://doi.org/10.1021/cr00002a004
  21. Fischer, A.; Galloway, W. J.; Vaughan, J. J. Chem. Soc. 1964, 3588 https://doi.org/10.1039/jr9640003588
  22. Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963 https://doi.org/10.1021/ja00463a032
  23. Castro, E. A.; Angel, M.; Arellano, D.; Santos, J. G. J. Org. Chem. 2001, 66, 6571 https://doi.org/10.1021/jo0101252
  24. Castro, E. A.; Leandro, L.; Millan, P.; Santos, J. G. J. Org. Chem. 1999, 64, 1953 https://doi.org/10.1021/jo982063u
  25. Stefanidas, D.; Cho, S.; Dhe-Paganon, S.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 1650 https://doi.org/10.1021/ja00058a006
  26. Fersht, A. R.; Jencks, W. P. J. Am. Chem. Soc. 1970, 92, 6963
  27. Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1989, 111, 2647 https://doi.org/10.1021/ja00189a045
  28. Colthurst, M. J.; Nanni, M.; Williams, A. J. Chem. Soc. Perkin Trans. 2 1996, 2285
  29. Pross, A. Adv. Phys. Org. Chem. 1997, 14, 69
  30. Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529 https://doi.org/10.1135/cccc19991529

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