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

Aleksey V Zerov; Galina L Starova; Vitalii V Suslonov; Olesya V Khoroshilova; Aleksander V Vasilyev

doi:10.1021/acs.orglett.7b03920

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

Org Lett. 2018 Feb 2;20(3):784-787. doi: 10.1021/acs.orglett.7b03920. Epub 2018 Jan 17.

Authors

Aleksey V Zerov¹, Galina L Starova², Vitalii V Suslonov², Olesya V Khoroshilova², Aleksander V Vasilyev^{1

3}

Affiliations

¹ Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University , Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.
² Research Center for X-ray Diffraction Studies, Research Park, St. Petersburg State University , Universitetskiy pr. 26, Saint Petersburg, Petrodvoretz 198504, Russia.
³ Department of Chemistry, Saint Petersburg State Forest Technical University , Institutskiy per. 5, Saint Petersburg 194021, Russia.

PMID: 29341618
DOI: 10.1021/acs.orglett.7b03920

Abstract

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.