Synthesis of 1-(tetrafluorophenyl)perfluoro-1-phenylethanes and their cyclization into polyfluoro-9-methylfluorenes under the action of antimony pentafluoride

Synthesis of 1-(tetrafluorophenyl)perfluoro-1-phenylethanes and their cyclization into polyfluoro-9-methylfluorenes under the action of antimony pentafluoride Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2020, Том: 237, Номер статьи : 109615, Страниц : 1 DOI: 10.1016/j.jfluchem.2020.109615

Ключевые слова

1,1-Diphenylethane; Cation; Cyclization; DFT calculations; Fluorene; Perfluorinated

Авторы

Mezhenkova T.V. ¹ , Komarov V.V. ¹ , Karpov V.M. ¹ , Beregovaya I.V. ¹ , Zonov Y.V. ¹

Организации

1	(Scopus) N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Novosibirsk, 630090, Russian Federation

The interaction of perfluoroethylbenzene with isomeric tetrafluorobenzenes in the presence of SbF5 at 25 °C, with further treatment of the reaction mixture with HF–pyridine and then with water, gives the corresponding 1-(tetrafluorophenyl)perfluoro-1-phenylethanes. 1-(2,3,4,5-Tetrafluorophenyl)perfluoro-1-phenylethane heated with SbF5 at 50–55 °C gives perfluoro-9-methylfluorene. 1-(2,3,5,6-Tetrafluorophenyl)perfluoro-1-phenylethane under similar conditions forms 1,2,3,4,5,7,8,9-octafluoro-9-(trifluoromethyl)fluorene and the corresponding 2,3,4,9-tetrahydro-1H-fluorene. In the case of 1-(2,3,4,6-tetrafluorophenyl)perfluoro-1-phenylethane, fluorene derivatives were not obtained under the action of SbF5 at 50–130 °C. The experimental data are consistent with the DFT calculations (B3LYP/6-31G*) of the energy barrier for the conrotatory electrocyclization of polyfluorinated 1,1-diphenyl-1-ethyl cations. © 2020 Elsevier B.V.

Mezhenkova T.V. , Komarov V.V. , Karpov V.M. , Beregovaya I.V. , Zonov Y.V.
Synthesis of 1-(tetrafluorophenyl)perfluoro-1-phenylethanes and their cyclization into polyfluoro-9-methylfluorenes under the action of antimony pentafluoride
Journal of Fluorine Chemistry. 2020. V.237. 109615 :1-1. DOI: 10.1016/j.jfluchem.2020.109615 WOS Scopus РИНЦ

Поступила в редакцию:	9 июн. 2020 г.
Принята к публикации:	23 июл. 2020 г.
Опубликована online:	26 июл. 2020 г.
Опубликована в печати:	1 сент. 2020 г.

Web of science	WOS:000560728900008
Scopus	2-s2.0-85089079748
РИНЦ	45360356
OpenAlex	W3044727119