대한화학회지 (Journal of the Korean Chemical Society)

  • 제47권3호
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  • Pages.229-236
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  • 2003
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  • 1017-2548(pISSN)
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  • 2234-8530(eISSN)
대한화학회 (Korean Chemical Society)
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Cyclobutenediones 에서 Butenolides로의 이색적인 반응

Unusual Transformation of Cyclobutenediones into Butenolides

  • 이관희 (한동대학교 생명식품과학부) ;
  • Kwan Hee Lee (School of Life and Food Science, Handong University) ;
  • Harold W. Moore (Department of Chemistry, University of California)
  • 발행 : 2003.06.20
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초록

Cyclobutenedions을 lithium trimethylsilylacetylene과 반응시키고 물로 반응을 정지시키면 butenolides가 생성된다. 이 색다른 반응을 위해 allene을 intermediate로 하는 기전을 제안하였다. 이는 trimethylsilyl group이 너무 크기 때문에 보통의 diradical intermediate는 형성이 어렵고, allene이 ${\alpha}$-silyl group에 의해 안정화되기 때문이라고 사료된다.

Butenolides are prepared from cyclobutenediones when cyclobutenediones are treated with lithium trimethylsilylacetylene, and quenched with water. A plausible mechanism, which contains an allene as an intermediate, is proposed. The usual diradical intermediate may not be formed because of the bulkiness of trimethylsilyl group, and the allenic intermediate may be stabilized by the ${\alpha}$-silyl group.

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참고문헌

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