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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 47, Number 3
JKCSEZ 47(3)
June 20, 2003 

 
Title
Unusual Transformation of Cyclobutenediones into Butenolides

Cyclobutenediones 에서 Butenolides로의 이색적인 반응
Author
Kwan Hee Lee, Harold W. Moore

이관희, Harold W. Moore
Keywords
뷰티놀라이드, 사이클로 뷰틴다이온, 알렌 , Butenolides, Cyclobutendiones, Allene
Abstract
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 α-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 α-silyl group.

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