대한화학회지 (Journal of the Korean Chemical Society)

  • 제36권2호
  • /
  • Pages.301-304
  • /
  • 1992
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  • 1017-2548(pISSN)
  • /
  • 2234-8530(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지

사카르보닐철산염, $HFe(CO)_4^-$을 이용한 아디파알데히드와 페닐렌디아민으로부터 과수소아제피노벤젠의 편리한 합성

The Facile Synthesis of Pyrrolidinobenzenes from Adipaldehyde and Phenylenediamine using$HFe(CO)_4^-$

  • Sang Chul Shim (Department of Industrial Chemistry, Kyungpook National University) ;
  • Byung Won Woo (Department of Industrial Chemistry, Kyungpook National University) ;
  • Chil Hoon Doh (Department of Industrial Chemistry, Kyungpook National University) ;
  • Dong Yup Lee (Department of Industrial Chemistry, Kyungpook National University) ;
  • Young Zoo Youn (Department of Industrial Chemistry, Kyungpook National University)
  • 발행 : 1992.04.20
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초록

에탄올성 사카르보닐철산염, $HFe(CO)_4^-$과 아디파알데히드를 조합하면 아미노기를 과수소아제핀고리로 선택적으로 전환을 하는데 매우 효과적이다. 페닐렌디아민은 상압의 일산화탄소, 상온, 및 철산염 존재하에서 아디파알데히드와 반응하여 대응하는 과수소아제핀을 보통의 수득율로 주었다. 이 반응에 철산염아디파알데히드-페닐렌디아민계에서 몰비가 1.0 : 1.0 : 1.0일 때는 한 개의 과수소아제핀고리를, 1.0 : 2.0 : 1.0의 경우에는 두 개의 과수소아제핀고리를 선택적으로 주었다.

Ethanolic tetracarbonylhydridoferrate, $HFe(CO)_4^-$, combined with adipaldehyde is very efficient for the selective transformation of an amino group into a perhydroazepine ring. Phenylenediamines react with adipaldehyde in the presence of $HFe(CO)_4^-$at room temperature under the atmospheric pressure of carbon monoxide to give the corresponding perhydroazepines in moderate yields. In these reactions, the molar ratio of 1.0 : 1.0 : 1.0 of the ferrate-adipaldehyde-phenylenediamine system gave one perhydroazepine ring, and the case of 1.0 : 2.0 : 1.0 gave two perhydroazepine rings, selectively.

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참고문헌

  1. J. Synth. Chem. Jpn. v.36 T. Kamiyama;M. Inoue;S. Enomoto
  2. Chem. Abst. v.76 C. Dupre;M. Cartinovis
  3. Chem. Abst. v.72 K. Farhat
  4. Chem. Abst. v.74 M. Bottu
  5. J. Am. Chem. Soc. v.71 P. Krumholz;H. M. Stettiner
  6. Bull. Chem. Soc. Jpn. v.48 Y. Watanabe;T. Mitsudo;M. Yamashita;Y. Takegami
  7. Bull. Chem. Soc. Jpn. v.48 Y. Takegami;Y. Watanabe;I. Kanaya;T. Mitsudo;H. Masada
  8. J. Org. Chem. v.37 R. Noyon;I. Umeda;T. Ishigami
  9. J. Org. Chem. v.41 H. Alper
  10. Tetrahedron Lett. S. C. Shim;K. N. Choi
  11. Tetrahedron v.42 S. C. Shim;K. T. Huh;W. H. Park
  12. Bull. Chem. Soc. Jpn. v.49 Y. Watanabe;S. C. Shim;T. Mitsudo;M. Yamashita;Y. Takegam
  13. J. Heterocyclic Chem. v.25 S. C. Shim;K. D. Kim;C. H. Doh;T. J. Kim;H. K. Lee
  14. J. Am. Chem. Soc. v.79 J. English;G. W. Barber
  15. Bull. Chem. Soc. Jpn. v.49 Y. Watanabe;S. C. Shim;T. Mitsudo;M. Yamashita;Y. Takegami