• Title/Summary/Keyword: Carbocyclization

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Studies Towards Intramolecular Formal Iron-Catalyzed [4+2] Cycloaddition of Acetylenic Dienes (Fe(0) 촉매를 이용한 Acetylenic Dienes 의 분자내 [4+2] 고리화 첨가반응에 관한 연구)

  • Byeon, Sang Yong
    • Journal of the Korean Chemical Society
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    • v.38 no.1
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    • pp.61-68
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    • 1994

  • The intramolecular formal iron-catalyzed [4+2] cycloaddition reaction of acetylenic dienes to produce bicyclic products has been investigated. These reactions proceeded, competing via intramolecular carbocyclization and bimolecular cycloaddition. However, the iron-catalyzed bicyclic carbocyclization of 4,4-dimethyl-3-(tert-butyldimethylsiloxy)-1-phenyl-6,8-decadien-1-yne(11) yielded exclusively bicyclic diene product(yield 78.1%). From this result, we found that the substrate containing a dimethyl substitutent at the 4,4-position helped to promote the intramolecular reaction, which is stable to the iron catalyzed conditions.

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