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Nucleophilic Substitution Reactions of Thiophenyl Cyclobutanecarboxylates with Benzylamines 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 : 2007.12.20

Abstract

Keywords

References

  1. Jencks, W. P. Chem. Rev. 1985, 85, 511 https://doi.org/10.1021/cr00070a001
  2. Oh, H. K.; Shin, C. H.; Lee, I. J. Chem. Soc. Perkin Trans. 2 1995, 1169
  3. Oh, H. K.; Shin, C. H.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 657
  4. Oh, H. K.; Yang, J. H.; Lee, I. Int. J. Chem. Kinet. 2000, 32, 485 https://doi.org/10.1002/1097-4601(2000)32:8<485::AID-KIN6>3.0.CO;2-X
  5. Oh, H. K.; Kim, S. K.; Cho, I. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 2000, 2306
  6. Oh, H. K.; Kim, S. K.; Lee, H. W.; Lee, I. New J. Chem. 2001, 25, 313 https://doi.org/10.1039/b006974o
  7. Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1
  8. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992
  9. Cullum, N. R.; Renfrew, A. H.; Rettura, J. A.; Taylor, J. A.; Whitmore, J. M. J.; Williams, A. J. Am. Chem. Soc. 1995, 117, 9200 https://doi.org/10.1021/ja00141a012
  10. Gresser, M.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963, 6970 https://doi.org/10.1021/ja00463a032
  11. Castro, E. A.; Ureta, C. J. Org. Chem. 1989, 54, 2153 https://doi.org/10.1021/jo00270a026
  12. Castro, E. A.; Ureta, C. J. Org. Chem. 1990, 55, 1676 https://doi.org/10.1021/jo00292a051
  13. Cabrera, M.; Castro, E. A.; Salas, M.; Santos, J. G.; Sepulveda, P. J. Org. Chem. 1991, 56, 5324 https://doi.org/10.1021/jo00018a022
  14. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451 https://doi.org/10.1021/ja00444a023
  15. Jensen, J. L.; Jencks, W. P. J. Am. Chem. Soc. 1979, 101, 1476 https://doi.org/10.1021/ja00500a019
  16. Dauglass, K. T. Acc. Chem. Res. 1989, 54, 2153
  17. Lee, I. Chem. Soc. Rev. 1994, 24, 223 https://doi.org/10.1039/cs9952400223
  18. Iaacs, N. S. Physical Organic Chemistry, 2nd ed.; Longman Harlow: 1995; p 186
  19. Lee, H. W.; Yun, Y. S.; Lee, B. S.; Koh, H. J.; Lee, I. J. Chem. Soc. Perkin. Trans. 2 2000, 2302
  20. Oh, H. K.; Woo, S. Y.; Oh, C. H.; Park, Y. S.; Lee, I. J. Org. Chem. 1997, 62, 5780 https://doi.org/10.1021/jo970413r
  21. Koh, H. J.; Han, K. L.; Lee, I. J. Org. Chem. 1999, 64, 478 https://doi.org/10.1021/jo9814748
  22. Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529 https://doi.org/10.1135/cccc19991529
  23. Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57
  24. Guggenheim, E. A. Phil. Mag. 1926, 2, 538 https://doi.org/10.1080/14786442608564083
  25. Oh, H. K.; Oh, J. Y. Bull. Korean Chem. Soc. 2006, 27, 143 https://doi.org/10.5012/bkcs.2006.27.1.143
  26. Oh, H. K.; Ku, M. H.; Lee, H. W. Bull. Korean Chem. Soc. 2005, 26, 935 https://doi.org/10.5012/bkcs.2005.26.6.935

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