Reactions of 1,5-Diaryl-3-(trifluoromethyl)pent-1-en-4-yn-3-yl Cations with Benzene in TfOH. Synthesis of CF-"Helicopter"-Like Molecules.

Org Lett

Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University , Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.

Published: February 2018

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

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http://dx.doi.org/10.1021/acs.orglett.7b03920DOI Listing

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