Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Zn(II)-catalyzed Rearrangement of Epoxides Using an Ionic Liquid

  • Ko, Nan-Hee (Department of Chemistry and Research Institute for Basic Sciences, Kyung Hee University) ;
  • Kim, Hoon-Sik (Department of Chemistry and Research Institute for Basic Sciences, Kyung Hee University) ;
  • Kang, Sang-Ook (Department of Chemistry, Korea University) ;
  • Cheong, Min-Serk (Department of Chemistry and Research Institute for Basic Sciences, Kyung Hee University)
  • Published : 2008.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155
  2. Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 733
  3. Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1968, 90, 4193 https://doi.org/10.1021/ja01017a071
  4. Stork, G.; Schulenberg, J. W. J. Am. Chem. Soc. 1962, 84, 284 https://doi.org/10.1021/ja00861a031
  5. Eliel, E. L.; Delmonte, D. W. J. Am. Chem. Soc. 1958, 80, 1744 https://doi.org/10.1021/ja01540a060
  6. House, H. O. J. Am. Chem. Soc. 1955, 77, 3070 https://doi.org/10.1021/ja01616a041
  7. House, H. O. J. Am. Chem. Soc. 1955, 77, 5083 https://doi.org/10.1021/ja01624a040
  8. Vankar, Y. D.; Saksena, R. K.; Bawa, A. Chem. Lett. 1989, 1241
  9. Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1971, 93, 1693 https://doi.org/10.1021/ja00736a021
  10. Naqvi, S. M.; Horwitz, J. P.; Filler, R. J. Am. Chem. Soc. 1957, 79, 6283 https://doi.org/10.1021/ja01580a046
  11. House, H. O. Org. Synthesis. Coll. Vol. IV, 1973, 375
  12. Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1997, 62, 6547 https://doi.org/10.1021/jo970743b
  13. Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195 https://doi.org/10.1021/jo00103a005
  14. Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212 https://doi.org/10.1021/jo980793w
  15. Karamé, I.; Tommasino, M. L.; Lemaire, M. Tetrahedron Lett. 2003, 44, 7687 https://doi.org/10.1016/S0040-4039(03)01593-4
  16. Procopio, A.; Dalpozzo, R.; De Nino, A.; Nardi, M.; Sindona, G.; Tagarelli, A. Synlett 2004, 2633
  17. Banerjee, M.; Roy, U. K.; Sinha, P.; Roy, S. J. Organomet. Chem. 2005, 690, 1422 https://doi.org/10.1016/j.jorganchem.2004.12.008
  18. Anderson, A. M.; Blazek, J. M.; Garg, P.; Payne, B. J.; Mohan, R. S. Tetrahedron Lett. 2000, 41, 1527 https://doi.org/10.1016/S0040-4039(99)02330-8
  19. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41 https://doi.org/10.1016/0301-0104(73)80059-X
  20. Baerends, E. J.; Ros, P. Chem. Phys. 1973, 2, 52 https://doi.org/10.1016/0301-0104(73)80060-6
  21. Ravenek, W. Algorithms and Applications on Vector and Parallel Computers; te Riele, H. J. J., Dekker, T. J., van de Horst, H. A., Eds.; Elsevier: Amsterdam, The Netherlands, 1987
  22. Velde, G.; Baerends, E. J. J. Comput. Chem. 1992, 99, 84
  23. Boerrigter, P. M.; Velde, G. t.; Baerends, E. J. Int. J. Quantum Chem. 1988, 33, 87 https://doi.org/10.1002/qua.560330204
  24. Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322 https://doi.org/10.1063/1.454603
  25. Snijders, J. G.; Baerends, E. J.; Vernoijs, P. At. Nucl. Data Tables 1982, 26, 483 https://doi.org/10.1016/0092-640X(81)90004-8
  26. Vernoijis, P.; Snijders, J. G.; Baerends, E. J. Slater Type Basis Functions for the Whole Periodic System; Internal Report (in Dutch); Department of Theoretical Chemistry, Free University: Amsterdam, The Netherlands, 1981
  27. Krijn, J.; Baerends, E. J. Fit Functions in the HFS Method; Internal Report (in Dutch); Department of Theoretical Chemistry, Free University: Amsterdam, The Netherlands, 1984
  28. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200 https://doi.org/10.1139/p80-159
  29. Becke, A. Phys. Rev. A 1988, 38, 3098 https://doi.org/10.1103/PhysRevA.38.3098
  30. Perdew, J. P. Phys. Rev. B 1986, 34, 7406
  31. Perdew, J. P. Phys. Rev. B 1986, 33, 8822 https://doi.org/10.1103/PhysRevB.33.8822
  32. Snijders, J. G.; Baerends, E. J. Mol. Phys. 1978, 36, 1789 https://doi.org/10.1080/00268977800102771
  33. Snijders, J. G.; Baerends, E. J.; Ros, P. Mol. Phys. 1979, 38, 1909 https://doi.org/10.1080/00268977900102941

Cited by

  1. Formation of Five- and Seven-Membered Rings Enabled by the Triisopropylsilyl Auxiliary Group vol.14, pp.1, 2012, https://doi.org/10.1021/ol203209b
  2. Gold(I)-Catalyzed Cyclodehydration Enabled by the Triisopropylsilyl Group: A Synthetically Versatile Methodology vol.95, pp.10, 2012, https://doi.org/10.1002/hlca.201200176
  3. Multifunctional Catalysis Promoted by Solvent Effects: Ti-MCM41 for a One-Pot, Four-Step, Epoxidation–Rearrangement–Oxidation–Decarboxylation Reaction Sequence on Stilbenes and Styrenes vol.5, pp.6, 2015, https://doi.org/10.1021/cs501671a
  4. ChemInform Abstract: Zn(II)-Catalyzed Rearrangement of Epoxides Using an Ionic Liquid. vol.39, pp.29, 2008, https://doi.org/10.1002/chin.200829094
  5. A Highly Regioselective and Practical Synthesis of α‐Aryl Ketones under a Cooperative Cascade Effect of an Ionic Liquid and Tetrabutylammonium Fluoride vol.8, pp.11, 2008, https://doi.org/10.1002/ajoc.201900513