Stable fluoroaliphatic radicals containing functional groups: Synthesis and reactivity

β-Fluorosulphatoperfluoroalkyl radicals ( 3, 7 and 8) are obtained by the reaction of fluoroolefins (HFP trimer and dimer, and perfluoro4 4-dimethylpent-2-ene, respectively) with (FSO 3) 2. The pure β-fluorosulphatotetrafluoroethylperfluorodiisopropylmethyl radical ( 3) has been isolated and convert...

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Published inJournal of fluorine chemistry Vol. 80; no. 2; pp. 77 - 80
Main Authors Sterlin, S.R., Cherstkov, V.F., Tumanskii, B.L., Avetisyan, E.A.
Format Journal Article
LanguageEnglish
Published LAUSANNE 1 Elsevier B.V 01.10.1996
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
ESR spectroscopy
Fluoroaliphatic radicals
Physical Sciences
Reactivity
Science & Technology
Synthesis
ESR spectroscopy
Synthesis
Reactivity
Fluoroaliphatic radicals
synthesis
reactivity
fluoroaliphatic radicals
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Summary:β-Fluorosulphatoperfluoroalkyl radicals ( 3, 7 and 8) are obtained by the reaction of fluoroolefins (HFP trimer and dimer, and perfluoro4 4-dimethylpent-2-ene, respectively) with (FSO 3) 2. The pure β-fluorosulphatotetrafluoroethylperfluorodiisopropylmethyl radical ( 3) has been isolated and converted to the perfluoroacetyldiisopropylmethyl radical ( 4) under the action of CsF. The reaction of radicals 3,7 and 8 with SbF 5 leads to the replacement of the FSO 3 group by a fluorine atom. The ability of the FSO 3 group in β-fluorosulphatoperfluoroalkyl radicals to play the role of a leaving group is explained by the stabilizing effect of the unshared electron on the adjacent carbocation centre.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(96)03491-4