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Interception of the radicals produced in electrophilic fluorination with radical traps (Tempo, Dmpo) studied by electrospray ionization mass spectrometry
Author(s) -
Zhang Xiang,
Wang Haoyang,
Guo Yinlong
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2532
Subject(s) - chemistry , radical , adduct , radical ion , photochemistry , electrospray ionization , electrophile , mass spectrometry , selectfluor , nitroxide mediated radical polymerization , cationic polymerization , medicinal chemistry , ion , organic chemistry , reagent , chromatography , radical polymerization , catalysis , polymer , copolymer
The interaction of the nitroxide radical traps (Tempo and Dmpo) and radicals produced in the electrophilic fluorination of olefins (styrene and α ‐methylstyrene) and Selectfluor (1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate) (F‐TEDA‐BF 4 ) (1)) was investigated by electrospray ionization mass spectrometry (ESI‐MS). Tempo succeeded in intercepting the radical cationic intermediates and the radical adduct ions were detected at m/z 260 (for styrene) and m/z 274 (for α ‐methylstyrene). Dmpo could also intercept the fluorine radical and radical adduct ions were detected at m/z 131, 132 and 152. The interception of the radical cationic intermediates and fluorine radical is good evidence for the presence of a single‐electron transfer mechanism in the electrophilic fluorination. Copyright © 2006 John Wiley & Sons, Ltd.