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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 23, Number 2
JKCSEZ 23(2)
April 20, 1979 

Reductive Amination of α,β-Unsaturated Carbonyl Compounds with Tetracarbonylhydridoferrate as a Reducing Agent

α,β-불포화 카르보닐화합물의 환원 아미노화반응
Hong-Seok Kim, Sang Chul Shim, Sang Chull Shim

김홍석, 심상철, 심상철
세개의 α,β-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 α,β-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.

The reductive amination of three α,β-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 α,β-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.

99 - 103
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