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Reaction of C,N -diphenylnitrone with octatluorobut-2-ene and octafluoronorbornadiene at room temperature affords the corresponding isoxazolidines ( 8 ) (96%) and ( 9 ) (28%), respectively; perfluoro-(2,3-dimethylbut-2-ene) and octafluorocyclopentene are unreactive under comparable conditions. Rearranged 1:1 adducts, i.e. C -pttenyl- C -(2-hydroxytetrafluorophenyl)imines ( 10 ), are formed from reaction of tetrafluorobenzync with the nitrones PhCH= + NR—O − (R=Ph, Bu t and Me), although the t-butylnitrone reaction also gives the benzo[ b ]isoxazolidine ( 11 ). The imine 10c formed from the methylnitrone is converted into an unidentified fibrous 1:1 adduct on attempted recrystallization [EtOH] and this hydrolyses readily to 2-hydroxytetrafluorobenzophenone ( 13 ). |
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