Bulletin of the Korean Chemical Society

  • 제15권10호
  • /
  • Pages.845-849
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  • 1994
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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
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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

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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