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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 CF 3 -"Helicopter"-Like Molecules.

Organic Letters 2018 Februrary 3
Trimethylsilyl ethers of 1,5-diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-oles in superacid CF3 SO3 H (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.

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