Bis(perfluoroorganyl)bromonium salts [(R-F)(2)Br]Y (R-F = aryl, alkenyl, and alkynyl)

Bis(perfluoroorganyl)bromonium salts [(R-F)(2)Br]Y (R-F = aryl, alkenyl, and alkynyl) Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2010, Volume: 131, Number: 9, Pages: 922-932 Pages count : DOI: 10.1016/j.jfluchem.2010.06.006

Tags

Bromine trifluoride; Perfluoroorganylbromine difluorides; Bis(perfluoroorganyl)bromonium salts; Difluorobromonium salts; Perfluoroorganylboron difluoride; Tris(pentafluorophenyl)borane; Pentafluorophenyltrifluorosilane; Pentafluorophenyltrimethylsilane; Perfluoroorganyltrifluoroborate salts; NMR spectroscopy

Authors

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

Affiliations

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

Bromonium salts [(RF)(2)Br]Y with perfluorinated groups R-F=C6F5, CF3CF=CF, C2F5CF=CF, and CF3C C were isolated from reactions of BrF3 with RFBF2 in weakly coordinating solvents (wcs) like CF3CH2CHF2 (PFP) or CF3CH2CF2CH3 (PFB) in 30-90% yields. C6F5BF2 formed independent of the stoichiometry only [(C6F5)(2)Br][BF4]. 1:2 reactions of BrF3 and silanes C6F5SiY3 (Y = F, Me) ended with different products - C6F5BrF2 or [(C6F5)(2)Br][SiF5] - as pure individuals, depending on Y and on the reaction temperature (Y = F). With C6F5SiF3 at >=-30 degrees C [(C6F5)(2)Br][SiF5] resulted in 92% yield whereas the reaction with less Lewis acidic C6F5SiMe3 only led to C6F5BrF2 (58%). The interaction of K[C6F5BF3] with BrF3 or [BrF2][SbF6] in anhydrous HF gave [(C6F5)(2)Br][SbF6]. Attempts to obtain a bis(perfluoroalkyl)bromonium salt by reactions of C6F13BF2 with BrF3 or of K[C6F13BF3] with [BrF2][SbF6] failed. The 3:2 reactions of BrF3 with (C6F5)(3)B in CH2Cl2 gave [(C6F5)(2)Br][(C6F5)(n)BF4-n] salts (n = 0-3). The mixture of anions could be converted to pure [BF4](-) salts by treatment with BF3.base. (C) 2010 Elsevier B.V. All rights reserved.

Frohn H-J. , Giesen M. , Welting D. , Bardin V.V.
Bis(perfluoroorganyl)bromonium salts [(R-F)(2)Br]Y (R-F = aryl, alkenyl, and alkynyl)
Journal of Fluorine Chemistry. 2010. V.131. N9. P.922-932. DOI: 10.1016/j.jfluchem.2010.06.006 WOS Scopus РИНЦ

Published print:

Sep 1, 2010

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