New types of asymmetrical bromonium salts [R-F(R-F ')Br]Y where R-F and/or R-F ' represent perfluorinated aryl, alkenyl, and alkynyl groups

New types of asymmetrical bromonium salts [R-F(R-F ')Br]Y where R-F and/or R-F ' represent perfluorinated aryl, alkenyl, and alkynyl groups Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2010, Volume: 131, Number: 10, Pages: 969-974 Pages count : DOI: 10.1016/j.jfluchem.2010.06.022

Tags

Bis(perfluoroorganyl)bromonium salts; Organyl(perfluoroorganyl)bromonium salts; Aryldifluorobromane; Perfluoroorganylboron difluorides; Aryltrifluorosilanes; NMR spectroscopy

Authors

Frohn Hermann-Josef ¹ , Giesen Matthias ¹ , Bardin Vadim V. ²

Affiliations

1	(Данные Web of science) Univ Duisburg Essen, Inst Inorgan Chem, Dept Chem, D-47048 Duisburg, Germany
2	(Данные Web of science) SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

A series of previously unknown asymmetrical fluorinated bis(aryl)bromonium, alkenyl(aryl)bromonium, and alkynyl(aryl)bromonium salts was prepared by reactions of C6F5BrF2 or 4-CF3C6H4BrF2 with aryl group transfer reagents Ar'SiF3 (Ar' = C6F5, 4-FC6H4, C6H5) or perfluoroorganyl group transfer reagents R-F'BF2 (R-F = C6F5, trans-CF3CF=CF, C3F7C C) preferentially in weakly coordinating solvents (CCl3F, CCl2FCClF2, CH2Cl2, CF3CH2CHF2(PFP), CF3CH2CF2CH3 (PFB)). The presence of the base MeCN and the influence of the adducts R-F'BF2 center dot NCMe (R-F = C6F5, CF3C C) on reactions aside to bromonium salt formation are discussed. Reactions of C6F5BrF2 with Alk(F)'BF2 in PFP gave mainly C6F5Br and Alk(F)'F (Alk(F)' = C6F13, C6F13CH2CH2), presumably, deriving from the unstable salts [C6F5(Alk(F)')Br]Y (Y = [Alk(F)'BF3](-)). Prototypical reactivities of selected bromonium salts were investigated with the nucleophile I- and the electrophile H+. [4-CF3C6H4(C6F5)Br][BF4] showed the conversion into 4-CF3C6H4Br and C6F5I when reacted with [Bu4N]I in MeCN. Perfluoroalkynylbromonium salts [CnF2n+1C C(R-F)Br][BF4] slowly added HF when dissolved in aHF and formed [Z-CnF2n+1CF=CH(R-F)Br][BF4]. (C) 2010 Elsevier B.V. All rights reserved.

Frohn H-J. , Giesen M. , Bardin V.V.
New types of asymmetrical bromonium salts [R-F(R-F ')Br]Y where R-F and/or R-F ' represent perfluorinated aryl, alkenyl, and alkynyl groups
Journal of Fluorine Chemistry. 2010. V.131. N10. P.969-974. DOI: 10.1016/j.jfluchem.2010.06.022 WOS Scopus РИНЦ

Published print:

Oct 1, 2010

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