Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations

Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2016, Volume: 192, Pages: 31-40 Pages count : 10 DOI: 10.1016/j.jfluchem.2016.10.009

Tags

Fluorinated; Benzocyclobutene; Indane; Perfluoroisopropyl group; Cation; DFT calculations

Authors

Mezhenkova Tatyana V. ¹ , Karpov Victor M. ¹ , Beregovaya Irina V. ¹ , Zonov Yaroslav V. ^1,2 , Chuikov Igor P. ¹ , Platonov Vyacheslav E. ¹

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

When perfluoro-1-alkylbenzocyclobutenes and -indanes were dissolved in an excess of SbF5, perfluorinated alkylbenzocycloalken-1-yl cations containing a fluorine atom or a perfluoroallcyl group in the cationic centre were generated. Contrary to expectations, a number of stable long-lived perfluoro-1-isopropylbenzocycloalken-1-yl cations containing an electron-withdrawing perfluoroisopropyl group in the cationic centre have been obtained. The DFT (B3LYP/6-31G*) calculations showed that the relative stabilities of isomeric cations containing a fluorine atom or a perfluoroalkyl group in the cationic centre change in favor of cations containing a perfluoroalkyl group in the cationic center when going from a CF3 to a CF(CF3)(2) group. This is in accordance with the experimental data. (C) 2016 Elsevier B.V. All rights reserved.

Mezhenkova T.V. , Karpov V.M. , Beregovaya I.V. , Zonov Y.V. , Chuikov I.P. , Platonov V.E.
Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations
Journal of Fluorine Chemistry. 2016. V.192. P.31-40. DOI: 10.1016/j.jfluchem.2016.10.009 WOS Scopus РИНЦ

Published print:

Dec 1, 2016

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