1255383-10-8Relevant articles and documents
New types of asymmetrical bromonium salts [RF(R F′)Br]Y where RF and/or RF′ represent perfluorinated aryl, alkenyl, and alkynyl groups
Frohn, Hermann-Josef,Giesen, Matthias,Bardin, Vadim V.
, p. 969 - 974 (2010)
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-CF3C 6H4BrF2 with aryl group transfer reagents Ar′SiF3 (Ar′ = C6F5, 4-FC 6H4, C6H5) or perfluoroorganyl group transfer reagents RF′BF2 (RF = C 6F5, trans-CF3CFCF, C3F 7C≡C) preferentially in weakly coordinating solvents (CCl 3F, CCl2FCClF2, CH2Cl2, CF3CH2CHF2 (PFP), CF3CH 2CF2CH3 (PFB)). The presence of the base MeCN and the influence of the adducts RF′BF2·NCMe (RF = C6F5, CF3C≡C) on reactions aside to bromonium salt formation are discussed. Reactions of C 6F5BrF2 with AlkF′BF 2 in PFP gave mainly C6F5Br and Alk F′F (AlkF′ = C6F13, C6F13CH2CH2), presumably, deriving from the unstable salts [C6F5(AlkF′)Br]Y (Y = [AlkF′BF3]-). Prototypical reactivities of selected bromonium salts were investigated with the nucleophile I-and the electrophile H+. [4-CF3C 6H4(C6F5)Br][BF4] showed the conversion into 4-CF3C6H4Br and C 6F5I 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+1CFCH(RF)Br][BF4].