Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Convenient and Efficient Method for Demethylation of Aryl Methyl Ethers with Magnesium Iodide in Ionic Liquid

  • Lee, Kwan-Soo (Department of Chemistry, KAIST) ;
  • Kim, Kee-D. (Department of Fine Chemical and Advanced Materials, Sangji University)
  • Received : 2010.08.25
  • Accepted : 2010.09.29
  • Published : 2010.12.20
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Abstract

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References

  1. Wuts, P. G. M.; Green, T. W. Greens’s Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons: New Jersey, 2007; p 370 and references therein.
  2. Maercker, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 972. https://doi.org/10.1002/anie.198709721
  3. Parker, K. A.; Petraitis, J. J. Tetrahedron Lett. 1981, 22, 397. https://doi.org/10.1016/0040-4039(81)80109-8
  4. Miller, J. M.; So, K. H.; Clark, J. H. Can. J. Chem. 1979, 57, 1887. https://doi.org/10.1139/v79-299
  5. Yadav, J. S.; Reddy, B. V. S.; Madan, C.; Hashim, S. R. Chem. Lett.2000, 29, 738.
  6. Dodge, J. A.; Stocksdale, M. G.; Fahey, K. J.; Jones, C. D. J. Org. Chem. 1995, 60, 739. https://doi.org/10.1021/jo00108a046
  7. Mechoulam, R.; Gaoni, Y. A. J. Am. Chem. Soc. 1965, 87, 3273.
  8. Majetich, G.; Zhang, Y.; Wheless, K. Tetrahedron Lett.1994, 35,8727. https://doi.org/10.1016/S0040-4039(00)78482-6
  9. Yamaguchi, S.; Sugiura, K.; Fukuoka, R.; Okazaki, K.; Takeuchi,M.; Kawase, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3607. https://doi.org/10.1246/bcsj.57.3607
  10. Yamaguchi, S.; Nedachi, M.; Yokoyama, H.; Hirai, Y. Tetrahedron Lett. 1999, 40, 7363. https://doi.org/10.1016/S0040-4039(99)01411-2
  11. Snyder, S. A.; Tang, Z.-Y.; Gupta, R. J. Am. Chem. Soc. 2009, 131, 5744. https://doi.org/10.1021/ja9014716
  12. Lourenço, N. M. T.; Afonso, C. A. M. Tetrahedron 2003, 59, 789. https://doi.org/10.1016/S0040-4020(02)01621-6
  13. Judeh, Z. M. A.; Shen, H.-Y.; Chi, B. C.; Feng, L.-C.; Selvasothi,S. Tetrahedron Lett. 2002, 43, 9381. https://doi.org/10.1016/S0040-4039(02)02327-4
  14. Boovanahalli, S. K.; Kim, D. W.; Chi, D. Y. J. Org. Chem. 2004,69, 3340. https://doi.org/10.1021/jo035886e

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