Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Reductive Amination of ${\alpha}$,${\beta}$-Unsaturated Carbonyl Compounds with Tetracarbonylhydridoferrate as a Reducing Agent

${\alpha}$,${\beta}$-不飽和 카르보닐化合物의 還元 아미노화反應

  • Kim Hong-Seok (Department of Chemistry, Korea Advanced Institute of Science) ;
  • Shim Sang Chul (Department of Chemistry, Korea Advanced Institute of Science) ;
  • Shim Sang Chull (Department of Polymer Science, Engineering College, Kyungpook National University)
  • 김홍석 (韓國科學院 化學科) ;
  • 심상철 (韓國科學院 化學科) ;
  • 심상철 (慶北大學校 工科大學 高分子工學科)
  • Published : 1979.04.30
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Abstract

The reductive amination of three ${\alpha}$,${\beta}$-unsaturated aldehydes, cinnamaldehyde, crotonaldehyde, and acrolein are carried out successfully by tetracarbonylhydridoferrate in the presence of various primary amines. In a typical reaction, a mixture of potassium tetracarbonylhydridoferrate (22 mmole), an amine (22∼44 mole) and ${\alpha}$,${\beta}$-unsaturated aldehyde (22 mmole), in ethanol (30∼50 ml) was stirred for 9∼60 hours at room temperature under carbon monoxide atmosphere. All the products were characterized as secondary amines by mass, infrared, and nmr spectra as well as gas chromatographic data.

세개의 ${\alpha}$,${\beta}$-불포화알데히드, 신남알데히드, 크로톤알데히드, 아크로레인을 여러가지 일차 아민 존재하에서 테트라카르보닐철산염으로 환원시켜 상당히 다른 수득률로 N-알킬아민을 합성하였다. 보통, $KHFe(CO)_4$ (22mmole)와 일차아민(22∼44mmole)과 ${\alpha}$,${\beta}$-불포화 알데히드 (22mmole)를 에탄올 용매에 넣고 일산화탄소 분위기하에 실온에서 9∼60시간 자석 젓개로 저어주면 일산화탄소를 천천히 흡수하면서 반응이 진행된다. 생성물은 가스크로마토그래피, 질량분석스펙트럼, 핵자기공명스펙트럼, 적외선스펙트럼 등으로 그 구조를 알았다.

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