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Kinetics and Mechanism of the Aminolysis of Thiophenyl Cyclopentanecarboxylates 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)
  • 발행 : 2009.01.20

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참고문헌

  1. Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018. https://doi.org/10.1021/ja00829a034
  2. Johnson, S. L. Adv. Phy. Org. Chem. 1967, 5, 237. https://doi.org/10.1016/S0065-3160(08)60312-3
  3. O'Leary, M. H.; Marlier, J. F. J. Am. Chem. Soc. 1979, 101, 3300. https://doi.org/10.1021/ja00506a027
  4. Koh, H. J.; Lee, H. C.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 839.
  5. Castro, E. A.; Steinfort, G. B. J. Chem. Soc, Perkin Trans. 2 1983, 453. https://doi.org/10.1039/p19830000453
  6. Palling, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 4869. https://doi.org/10.1021/ja00329a040
  7. Castro, E. A.; Santander, C. L. J. Org. Chem. 1985, 50, 3595. https://doi.org/10.1021/jo00219a029
  8. Castro, E. A.; Ureta, C. J. Org. Chem. 1990, 55, 1676. https://doi.org/10.1021/jo00292a051
  9. Koh, H. J.; Shin, C. H.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1998, 1329.
  10. Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963, 6970.
  11. Bond, P. M.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1976, 679.
  12. Castro, E. A.; Gil, F. J. J. Am. Chem. Soc. 1977, 99, 7611. https://doi.org/10.1021/ja00465a032
  13. Castro, E. A.; Freudenberg, M. J. Org. Chem. 1980, 45, 906. https://doi.org/10.1021/jo01293a027
  14. Castro, E. A.; Ibanez, F.; Lagos, S.; Schick, M.; Santos, J. G. J. Org. Chem. 1992, 57, 2691. https://doi.org/10.1021/jo00035a028
  15. Castro, E. A.; Ibanez, F. ; Saitua, A. M.; Santos, J. G. J. Chem. Res. Synop. 1993, 56.
  16. Castro, E. A. Chem. Rev. 1999, 99, 3505. https://doi.org/10.1021/cr990001d
  17. Williams, A. Concerted Organic and Bio-organic Mechanisms; CRC Press: Boca Raton, 2000; Chapter 4.
  18. Castro, E. A.; Ibanez, F.; Salas, M.; Santos, J. G. J. Org. Chem. 1991, 56, 4819. https://doi.org/10.1021/jo00016a002
  19. Castro, E. A.; Salas, M.; Santos, J. G. J. Org. Chem. 1994, 59, 30. https://doi.org/10.1021/jo00016a002
  20. Oh, H. K.; Shin, C. H.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 657. https://doi.org/10.1021/jo00080a008
  21. Castro, E. A.; Munoz, P.; Santos, J. G. J. Org. Chem. 1999, 64, 8298. https://doi.org/10.1021/jo991036g
  22. Castro, E. A.; Leandro, L.; Millan, P.; Santos, J. G. J. Org. Chem. 1999, 64, 1953. https://doi.org/10.1021/jo991036g
  23. Skoog, M. T.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 7597. https://doi.org/10.1021/jo982063u
  24. Bourne, N.; Williams, A. J. Am. Chem. Soc. 1984, 106, 7591. https://doi.org/10.1021/ja00336a047
  25. Ba-Saif, S. A.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1989, 111, 2647. https://doi.org/10.1021/ja00336a046
  26. Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57. https://doi.org/10.1021/ja00189a045
  27. Lee, I. Chem. Soc. Rev. 1994, 24, 223. https://doi.org/10.1039/cs9952400223
  28. Lee, I.; Lee, H. W. Coll. Czech. Chem. Commun. 1999, 64, 1529. https://doi.org/10.1039/cs9952400223
  29. Oh, H. K.; Lee, J. Y.; Lee, H. W.; Lee, I. New J. Chem. 2002, 26, 473. https://doi.org/10.1135/cccc19991529
  30. Jeong, K. S.; Oh, H. K. Bull. Korean Chem. Soc. 2007, 28, 2535. https://doi.org/10.1039/b107403m
  31. Oh, H. K.; Woo, S. Y.; Shin, C. H.; Park, Y. S.; Lee, I. J. Org. Chem. 1997, 62, 5780. https://doi.org/10.5012/bkcs.2007.28.12.2535
  32. Koh, H. J.; Lee, J. W.; Lee, H. W.; Lee, I. Can. J. Chem. 1988, 76, 710. https://doi.org/10.1021/jo970413r
  33. Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 454. https://doi.org/10.1139/cjc-76-6-710
  34. Lee, I.; Kim, C. K.; Han, I. S.; Kim, W. K.; Kim, Y. B. J. Phys. Chem. B 1999, 103, 7302. https://doi.org/10.1021/jp991115w
  35. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. In ab initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4. https://doi.org/10.1021/jp991115w
  36. Yew, K. H.; Koh, H. J.; Lee, H. W.; Lee, I. J. Chem. Soc. Perkin Trans. 2 1995, 2263.
  37. Lee, H. W.; Yun, Y. S.; Lee, B. S.; Koh, H. J.; Lee, I. J. Chem. Soc. Perkin Trans. 2 2000, 2302.
  38. Koh, H. J.; Han, K. L.; Lee, I. J. Org. Chem. 1999, 64, 4783. https://doi.org/10.1021/jo990115p
  39. Koh, H. J.; Kim, S. I.; Lee, B. C.; Lee, I. J. Chem. Soc. Perkin Trans. 2 1996, 1353. https://doi.org/10.1021/jo990115p
  40. Lee, I.; Koh, H. J. New J. Chem. 1996, 20, 132.
  41. 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
  42. Oh, H. K.; Jeong, J. Bull. Korean Chem. Soc. 2001, 22, 1123. https://doi.org/10.1021/jo970413r
  43. Pross, A. Adv. Phys. Org. Chem. 1997, 14, 69.
  44. Jeong, K. S.; Oh, H. K. Bull. Korean Chem. Soc. 2008, 29, 675. https://doi.org/10.5012/bkcs.2008.29.3.675
  45. Guggenheim, E. A. Phil. Mag. 1926, 2, 538. https://doi.org/10.5012/bkcs.2008.29.3.675
  46. Jeong, K. S.; Oh, H. K. Bull. Korean Chem. Soc. 2007, 28, 485. https://doi.org/10.5012/bkcs.2007.28.3.485
  47. Oh, H. K.; Oh, J. Y. Bull. Korean Chem. Soc. 2006, 27, 143. https://doi.org/10.5012/bkcs.2007.28.3.485

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