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Pyridinolysis of Bis(N,N-dimethylamino) Phosphinic Chloride in Acetonitrile

  • Received : 2011.10.27
  • Accepted : 2011.11.07
  • Published : 2012.01.20

Abstract

Keywords

References

  1. Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12. https://doi.org/10.1021/jo990671j
  2. Lee, H. W.; Guha, A. K.; Kim, C. K.; Lee, I. J. Org. Chem. 2002, 67, 2215. https://doi.org/10.1021/jo0162742
  3. Adhikary, K. K.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 1135. https://doi.org/10.5012/bkcs.2003.24.8.1135
  4. Hoque, M. E. U.; Dey, N. K.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 1797. https://doi.org/10.5012/bkcs.2007.28.10.1797
  5. Adhikary, K. K.; Lumbiny, B. J.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 851. https://doi.org/10.5012/bkcs.2008.29.4.851
  6. Lumbiny, B. J.; Adhikary, K. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 1769. https://doi.org/10.5012/bkcs.2008.29.9.1769
  7. Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, H. W. J. Phys. Org. Chem. 2010, 23, 1022. https://doi.org/10.1002/poc.1709
  8. Dey, N. K.; Adhikary, K. K.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2010, 31, 3856. https://doi.org/10.5012/bkcs.2010.31.12.3856
  9. Dey, N. K.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 709. https://doi.org/10.5012/bkcs.2011.32.2.709
  10. Hoque, M. E. U.; Dey, S.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 1138. https://doi.org/10.5012/bkcs.2011.32.4.1138
  11. Guha, A. K.; Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 1375. https://doi.org/10.5012/bkcs.2011.32.4.1375
  12. Guha, A. K.; Kim, C. K.; Lee, H. W. J. Phys. Org. Chem. 2011, 24, 474. https://doi.org/10.1002/poc.1788
  13. Adhikary, K. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 1945. https://doi.org/10.5012/bkcs.2011.32.6.1945
  14. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 2109. https://doi.org/10.5012/bkcs.2011.32.6.2109
  15. Barai, H. R.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 2339. https://doi.org/10.5012/bkcs.2011.32.7.2339
  16. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 2805. https://doi.org/10.5012/bkcs.2011.32.8.2805
  17. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 3505. https://doi.org/10.5012/bkcs.2011.32.9.3505
  18. Adhikary, K. K.; Lumbiny, B. J.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 3743. https://doi.org/10.5012/bkcs.2011.32.10.3743
  19. Adhikary, K. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 3947. https://doi.org/10.5012/bkcs.2011.32.11.3947
  20. Barai, H. R.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 4179. https://doi.org/10.5012/bkcs.2011.32.12.4179
  21. Barai, H. R.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 4347. https://doi.org/10.5012/bkcs.2011.32.12.4347
  22. Taft, R. W. Steric Effect in Organic Chemistry; Newman, M. S., Ed.; Wiley: New York, 1956; Chapter 3.
  23. Exner, O. Correlation Analysis in Chemistry: Recent Advances; Chapman, N. B., Shorter, J.; Eds; Plenum Press: New York, 1978; p 439.
  24. Fischer, A.; Galloway, W. J.; Vaughan, J. J. Chem. Soc. 1964, 3591. https://doi.org/10.1039/jr9640003591
  25. Dean, J. A. Handbook of Organic Chemistry; McGraw-Hill: New York, 1987; Chapter 8.
  26. Castro, E. A.; Freudenberg, M. J. Org. Chem. 1980, 45, 906. https://doi.org/10.1021/jo01293a027
  27. Lee, I.; Kim, C. K.; Han, I. S.; Lee, H. W.; Kim, W. K.; Kim, Y. B. J. Phys. Chem. B 1999, 103, 7302. https://doi.org/10.1021/jp991115w
  28. Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 45. https://doi.org/10.1002/9780470171837.ch2
  29. Hehre, W. J.; Random, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4.
  30. Barai, H. R.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32
  31. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 1997. https://doi.org/10.5012/bkcs.2011.32.6.1997
  32. Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2009, 22, 425. https://doi.org/10.1002/poc.1478
  33. Dey, N. K.; Lee, H. W. Bull. Korean Chem. Soc. 2010, 31, 1403. https://doi.org/10.5012/bkcs.2010.31.5.1403
  34. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 936. https://doi.org/10.5012/bkcs.2007.28.6.936
  35. Williams, A. Free Energy Relationships in Organic and Bioorganic Chemistry; RSC: Cambridge, UK, 2003; Chapter 7.
  36. Ruff, A.; Csizmadia, I. G. Organic Reactions Equilibria, Kinetics and Mechanism; Elsevier: Amsterdam, Netherlands, 1994; Chapter 7.
  37. Oh, H. K.; Lee, J. M.; Lee H. W.; Lee, I. Int. J. Chem. Kinet. 2004, 36, 434. https://doi.org/10.1002/kin.20000
  38. Oh, H. K.; Park, J. E.; Lee, H. W. Bull. Korean Chem. Soc. 2004, 25, 1041. https://doi.org/10.5012/bkcs.2004.25.7.1041
  39. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 8995. https://doi.org/10.1021/jo0264269
  40. Castro, E. A.; Angel, M.; Campodonico, P.; Santos, J. G. J. Org. Chem. 2002, 67, 8911. https://doi.org/10.1021/jo026390k
  41. Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 2002, 67, 4494. https://doi.org/10.1021/jo0255532
  42. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 3874. https://doi.org/10.1021/jo025637a
  43. Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 2002, 67, 3129.
  44. Castro, E. A.; Pavez, P.; Arellano, D.; Santos, J. G. J. Org. Chem. 2001, 66, 6571. https://doi.org/10.1021/jo0101252
  45. Spillane, W. J.; McGrath, P.; Brack, C.; O'Byrne, A. B. J. Org. Chem. 2001, 66, 6313. https://doi.org/10.1021/jo015691b
  46. Koh, H. J.; Han, K. L.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 4706. https://doi.org/10.1021/jo000411y
  47. Humeres, E.; Debacher, N. A.; Sierra, M. M. D.; Franco J. D.; Shutz, A. J. Org. Chem. 1998, 63, 1598. https://doi.org/10.1021/jo971869b
  48. Baynham, A. S.; Hibbert, F.; Malana, M. A. J. Chem. Soc., Perkin Trans 2 1993, 1711.

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