Tetrabromobutatriene: completing the perhalocumulene series.
Tetrabromobutatriene: completing the perhalocumulene series.
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DOI：
10.1021/ol049734x
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发表时间：
2004-05
期刊：
影响因子：
5.2
通讯作者：
Pei-Hua Liu;Lei Li;Jeffrey A. Webb;Yi Zhang;N. Goroff
中科院分区：
文献类型：
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作者：
Pei-Hua Liu;Lei Li;Jeffrey A. Webb;Yi Zhang;N. Goroff
[结构：四溴丁三烯，C（4）Br（4），可以直接由二溴丁二炔与Br（2）在-25 ℃的浓己烷溶液中反应制备。从反应混合物中沉淀出黄色粉末状的累积多烯。在钯催化的偶联条件下，C（4）Br（4）可以发生烯丙基重排，得到混合物产物，包括一些具有丁烯炔骨架的产物。而在呋喃溶液中，C（4）Br（4）在其中心双键处发生干净的反应，生成呋喃Diels-Alder加成物。在Suzuki条件下，该加合物在呋喃双键处而不是在溴化物处反应。
[structure: see text] Tetrabromobutatriene, C(4)Br(4), can be prepared directly from dibromobutadiyne by reaction with Br(2) at -25 degrees C in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C(4)Br(4) can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C(4)Br(4) reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.