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Mono-dehalogenation of gem-Dihalocyclopropanes Using Tetracarbonylhydridoferrate

  • Shim, Sang-Chul (Department of Industrial Chemistry, Kyungpook National University) ;
  • Lee, Seung-Yub (Department of Industrial Chemistry, Kyungpook National University) ;
  • Lee, Dong-Yub (Department of Industrial Chemistry, Kyungpook National University) ;
  • Choi, Heung-Jin (Department of Industrial Chemistry, Kyungpook National University)
  • 발행 : 1994.10.20

초록

Tetracarbonylhydridoferrate, $HFe(CO)^-_4$, generated by the reaction of $Fe(CO)_5$ with alkaline solution, is a good reducing agent for mono-dehalogenation of gem-dihalocyclopropanes. It also acts as a good reducing catalyst under phase transfer reaction conditions. 1,1-Dibromo-2-phenylcyclopropane and 1,1-dichloro-2-phenylcyclopropane were reduced to the corresponding mono-dehalogenated products in excellent yields. Thermodynamically stable trans-l-bromo-2-phenyl cyclopropane was formed as the major product over the cis-isomer, trans/cis=3/2. The 1-bromo-2-phenyl cyclopropane radical intermediate was formed by single electron transfer from $HFe(CO)^-_4$. Dissociation of bromide anion, followed abstraction of hydrogen radical from alcoholic solvent would lead to the formation of the stable trans-isomer. The further mechanistic aspects were discussed.

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참고문헌

  1. J. Chem. Rev. v.90 Brunet, J.
  2. J. Org. Chem. v.52 Meijs, G. F.
  3. Bull. Chem. Soc. Jpn. v.57 Osuka, A.;Takechi, K.; Suzuki, H.
  4. Chem. Lett. Shimizu, N.;Watanabe, K.;Tsuno, Y.
  5. J. Org. Chem. v.31 Skattebol, S. J.
  6. Tetrahedron Lett. v.31 Reyne, R.;Burn, P.;Waegell, B.
  7. J. Am. Chem. Soc. v.88 Tobey, S. W.;West, R.
  8. J. Am. Chem. Soc. v.78 Skell, D. S.;Garner, A. Y.
  9. J. Org. Chem. v.31 Seyferth, D.;Prokai, B.
  10. J. Chem. Soc. D. Yamanaka, H.;Yagi, T.;Teramura, K.;Ando, T.
  11. Tetrahedron v.24 Kobrich, G.;Goyert, W.
  12. J. Org. Chem. v.28 Seyferth, D.;Yamazaki, H.;Alleston, D. L.
  13. Tetrahedron Lett. v.32 Masakzu, Y.;Rikisaku, S.
  14. J. Organomet. Chem. v.348 Brunet, J. J.;Taillerfer, M.
  15. Tetrahedron Lett. v.27 Alper, H.
  16. Bull. Chem. Soc. Jpn. v.50 Kitatani, K.;Hiyama, T.;Nozaki, H.
  17. J. Org. Chem. v.58 Haranda, T.;Katsuhira,T.;Hattori, K. A.
  18. Acc. Chem. Res. v.3 Cole, R. B.
  19. Bull. Chem. Soc. Jpn. v.40 Takegami, Y.;Watanabe, Y.;Mitsudo, T.;Okajima, T.
  20. J. Am. Chem. Soc. v.76 Doering, W. Von E.;Hoffmann, A. K.
  21. Chem. Lett. Mitsudo, T.;Watanabe, Y.;Yamashita, M.;Takegami, Y.
  22. Principles and Applications of Organotransition Metal Chemistry Collman, J. P.;Hegedus, L. S.;Norton, J. R.;Finke, R. G.
  23. Organometallics v.10 Brunet, J. J.;Montauzon, D.;Taillerfer, M.
  24. J. Organomet. Chem. v.218 Marko, L.;Radhi, M. A.;Otvos, I.

피인용 문헌

  1. ChemInform Abstract: Mono-Dehalogenation of gem-Dihalocyclopropanes Using Tetracarbonylhydridoferrate. vol.26, pp.20, 1995, https://doi.org/10.1002/chin.199520080
  2. Cp2TiCl2 Catalyzed Debromination of gem-Dibromocyclopropanes to Cyclopropanes by LiBH4 vol.49, pp.6, 1994, https://doi.org/10.5012/jkcs.2005.49.6.613
  3. Probes for Narcotic Receptor Mediated Phenomena. 41. Unusual Inverse μ-Agonists and Potent μ-Opioid Antagonists by Modification of the N-Substituent in Enantiomeric 5-(3-Hydroxyphenyl)morphans vol.54, pp.4, 1994, https://doi.org/10.1021/jm1011676