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Mono-dehalogenation of gem-Dihalocyclopropanes Using Tetracarbonylhydridoferrate
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  • Mono-dehalogenation of gem-Dihalocyclopropanes Using Tetracarbonylhydridoferrate
  • Mono-dehalogenation of gem-Dihalocyclopropanes Using Tetracarbonylhydridoferrate
저자명
Shim. Sang-Chul,Lee. Seung-Yub,Lee. Dong-Yub,Choi. Heung-Jin
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1994년|15권 10호|pp.845-849 (5 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

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.