Reactions of 1,5-Diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-yl Cations with Benzene in TfOH. Synthesis of CF3-“Helicopter”-Like Molecules,Organic Letters

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Reactions of 1,5-Diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-yl Cations with Benzene in TfOH. Synthesis of CF3-“Helicopter”-Like Molecules
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-17 00:00:00 , DOI: 10.1021/acs.orglett.7b03920
Aleksey V. Zerov ₁ , Galina L. Starova ₂ , Vitalii V. Suslonov ₂ , Olesya V. Khoroshilova ₂ , Aleksander V. Vasilyev _{1,

3}

Affiliation

Trimethylsilyl ethers of 1,5-diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-oles in superacid CF₃SO₃H (TfOH) give rise to the corresponding intermediate CF₃-pentenynyl cations. These species react with benzene to afford conjugated CF₃-pentenynes, which undergo subsequent cyclization, first, into CF₃-cycloheptadienes and, finally, into unusual CF₃-“helicopter”-like bicyclic structures.

中文翻译：

1，5-二芳基-3-（三氟甲基）戊-1-烯-4-yn-3-基阳离子与苯在TfOH中的反应。CF _3- “直升机”样分子的合成

在超酸CF ₃ SO ₃ H（TfOH）中的1,5-二芳基-3-（三氟甲基）戊-1-烯-4-yn-3-oles的三甲基甲硅烷基醚产生相应的中间体CF _3-戊炔基阳离子。这些物质与苯反应生成共轭CF _3-戊烯，随后经历环化反应，首先进入CF _3-环庚二烯，最后进入不寻常的CF _3- “直升机”状双环结构。

更新日期：2018-01-17

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