Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Selective and Efficient Deoxygenation of Amine-N-Oxides with CeCl3·7H2O/Zinc System

  • Yoo, Byung Woo (Department of Advanced Materials Chemistry, Korea University) ;
  • Jung, Ha Il (Department of Advanced Materials Chemistry, Korea University) ;
  • Kim, Se Heon (Department of Advanced Materials Chemistry, Korea University) ;
  • Ahn, Young Sun (Department of Advanced Materials Chemistry, Korea University) ;
  • Choi, Ji Yong (Department of Advanced Materials Chemistry, Korea University)
  • Received : 2012.10.26
  • Accepted : 2012.11.22
  • Published : 2013.02.20
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References

  1. Ochiai, E. In Aromatic Amine Oxides; Elsevier: Amsterdam, 1967; pp 184-209.
  2. Malinoswaki, M. Synthesis 1987, 732.
  3. Balicki, R. Chem. Ber. 1990, 647.
  4. Balicki, R.; Kaczmarek, L.; Malinnowski, M.Synth. Commun. 1989, 19, 897. https://doi.org/10.1080/00397918908051009
  5. Yoo, B. W.; Choi, J. W.; Kim, D. Y.; Hwang, S. K.; Choi, K. I.; Kim, J. H. Bull. Korean Chem. Soc. 2002, 23, 797. https://doi.org/10.5012/bkcs.2002.23.6.797
  6. Balick, R.; Cybulski, M.; Maciejewski, G. Synth. Commun. 1989, 19, 897. https://doi.org/10.1080/00397918908051009
  7. Ilias, M.; Barman, D. C.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 2002, 43, 1877. https://doi.org/10.1016/S0040-4039(02)00020-5
  8. Kozuka, S.; Akasaka, K.; Furumai, T.; Dae, S. Chem. Ind. (London) 1974, 452.
  9. Jousseaume, B.; Chanson, E. Synthesis 1987, 55.
  10. Balicki, R. Synthesis 1989, 645.
  11. Ilankumaran, P.; Chandrasekaran, S. Tetrahedron Lett. 1995, 36, 4881. https://doi.org/10.1016/0040-4039(95)00875-D
  12. Handa, Y.; Tanaka, W.; Ohta, A. J. Chem. Soc. Chem. Commun. 1994, 10, 1225.
  13. Yadav, J. S.; Reddy, B. V. S.; Reddy, M. M. Tetrahedron Lett. 2000, 41, 2663. https://doi.org/10.1016/S0040-4039(00)00218-5
  14. Yoo, B. W.; Choi, J. W.; Yoon, C. M. Tetrahedron Lett. 2006, 47, 125. https://doi.org/10.1016/j.tetlet.2005.10.143
  15. Singh, S. K.; Reddy, M. S.; Mangle, M.; Ganesh, K. R. Tetrahedron 2007, 63, 126. https://doi.org/10.1016/j.tet.2006.10.031
  16. Sanjay, K.; Anil, S.; Sandhu, J. S. Tetrahedron Lett. 2005, 46, 8737. https://doi.org/10.1016/j.tetlet.2005.10.047
  17. Saini, A.; Kumar, S.; Sandhu, J. S. Synlett 2006, 395.
  18. Yoo, B. W.; Choi, K. H.; Lee, S. J.; Yoon, C. M.; Kim, S. H.; Kim, J. H. Synth. Commun. 2002, 32, 63. https://doi.org/10.1081/SCC-120001509
  19. Yoo, B.W.; Lee, S. J.; Yoo, B. S.; Choi, K. I.; Kim, J. H. Synth. Commun. 2002, 32, 2489. https://doi.org/10.1081/SCC-120003398
  20. Yoo, B. W.; Min, S. K. Synth. Commun. 2011, 41, 2993. https://doi.org/10.1080/00397911.2010.516382
  21. Yoo, B. W.; Kim, D. I.; Kim, H. M.; Kim, S. H. Bull. Korean Chem. Soc. 2012, 33, 2851. https://doi.org/10.5012/bkcs.2012.33.9.2851
  22. Yoo, B. W.; Kim, S. H.; Min, G. H. Bull. Korean Chem. Soc. 2012, 33, 27. https://doi.org/10.5012/bkcs.2012.33.1.27
  23. Sarmah, B. K.; Barua, N. C. Tetrahedron 1991, 47, 8587. https://doi.org/10.1016/S0040-4020(01)82402-9
  24. Bezbarua, M. S.; Bez, G.; Barua, N. C. Chem. Lett. 1999, 325.
  25. Wang, W. B.; Shi, L. L.; Huang, Y. Z. Tetrahedron Lett. 1990, 31, 1185. https://doi.org/10.1016/S0040-4039(00)88761-4
  26. Barua, M.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1996, 37, 4559. https://doi.org/10.1016/0040-4039(96)00844-1
  27. B. Rama, R.; Gitali, D.; Yoofisaca, S. N.; Anil, K. S. Synlett 2005, 358.
  28. Molander, G. A. Chem. Rev. 1992, 92, 29. https://doi.org/10.1021/cr00009a002
  29. Imamoto, T. Lanthanides in Organic Synthesis, academic Press: London, 1994.
  30. Giuseppe, B.; Enrico, M.; Letizia, S. Synlett 2003, 2101.
  31. Katritzky, A. R.; Monro, A. M. J. Chem. Soc. 1958, 1263. https://doi.org/10.1039/jr9580001263
  32. Dictionary of Organic Compounds, 4th ed.; Pollock, J. R. A.; Stevens, R., Eds.; Eyre & Spottiswoode: London, 1965.

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