3512-11-6Relevant academic research and scientific papers
Synthesis of perfluorinated biaryls by reaction of perfluoroarylzinc compounds with perfluoroarenes
Vinogradov,Platonov
, p. 1388 - 1394 (2015)
Symmetrical and unsymmetrical perfluorinated biaryls have been synthesized by reactions of perfluorinated benzonitrile, nitrobenzene, toluene, m-xylene, and pyridine with perfluoroarylzinc compounds derived from chloropentafluorobenzene, octafluorotoluene
From hypervalent xenon difluoride and aryliodine(III) difluorides to onium salts: Scope and limitation of acidic fluoroorganic reagents in the synthesis of fluoroorgano xenon(II) and iodine(III) onium salts
Abo-Amer, Anwar,Frohn, Hermann-Josef,Steinberg, Christoph,Westphal, Ulrich
, p. 1311 - 1323 (2008/12/21)
Fluorinated organodifluoroboranes RfBF2 are in general suitable reagents to transform XeF2 and RIF2 into the corresponding onium tetrafluoroborate salts [RfXe][BF4] and [R(Rf)I][BF4], respectively. (4-C5F4N)BF2 and trans-CF3CF{double bond, long}CFBF2 which represent boranes of high acidity form no Xe-C onium salts in reactions with XeF2 but give the desired iodonium salts with RIF2 (R = C6F5, o-, m-, p-C6FH4). The reaction of (4-C5F4N)BF2 with XeF2 ends with a XeF2-borane adduct. C6F5Xe(4-C5F4N), the first Xe-(4-C5F4N) compound, was obtained when C6F5XeF was reacted with Cd(4-C5F4N)2. We describe the synthesis of (4-C5F4N)IF2 and reactions of (4-C5F4N)IF2 and C6F5IF2 with (4-C5F4N)BF2. Analogous to [(4-C5F4N)2I][BF4] and [C6F5(4-C5F4N)I][BF4] aryl(perfluoroalkenyl)iodonium salts [R(R′)I][BF4] were obtained from RIF2 (R = C6F5, o-, m-, p-C6FH4) and R′BF2 (R′ = trans-CF3CF{double bond, long}CF, CF2{double bond, long}CF). The gas phase fluoride affinities pF- of selected fluoroorganodifluoroboranes RfBF2 and their hydrocarbon analogs are calculated (B3LYP/6-31+G*) and discussed with respect to their potential to introduce Rf-groups into hypervalent EF2 bonds. Four aspects which influence the transformation of hypervalent EF2 bonds (E = Xe, R′I) under the action of Lewis acidic reagents RAFn-1 (A = B, P; n = 3, 5) into the corresponding [RE][AFn+1] salts are presented and the important role of the acidity is emphasized. Fluoride affinities may help to plan the introduction of organo groups into EF2 moieties and to expand the types of acidic reagents. Thus C6H5PF4 with a pF- value comparable to that of RfBF2 compounds is able to introduce the C6H5 group into RIF2 (R = C6F5, p-C6FH4).
Preparation, NMR spectra and reactivity of pentafluorophenyltetrafluorosilicates M+-
Frohn, H. J.,Bardin, V. V.
, p. 155 - 160 (2007/10/02)
Pentafluorophenyltetrafluorosilicates M+ - were obtained from pentafluorophenyltrifluorosilane C6F5SiF3 and ionic fluorides MF (M=K, Cs, Me4N) in anhydrous MeCN or diglyme.The reactivity of M+ - toward electrophiles was studied.Keywords: Pentafluorophenyl; Fluorosilicate anion; Desilylation
Use of tris(pentafluorophenyl)bismuth as an arylating reagent
Miller, A. O.,Furin, G. G.
, p. 168 (2007/10/02)
It has been shown that tris(pentafluorophenyl)bismuth arylates polyfluorinated electrophilic compounds in the presence of cesium fluoride. - Key words: tris(pentafluorophenyl)bismuth; cesium fluoride; perfluoro-2-methyl-2-pentene; perfluoro-5-aza-4-nonene
