About: Radical Additions to Fluoroolefins. Photochemical Mono-Fluoroalkylation and Sequential Bis-Fluoroalkylation of Oxolane.     Goto   Sponge   NotDistinct   Permalink

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  • Oxolane was fluoroalkylated by its photoadditions under atmospheric pressure. Monofluoro-alkylations were carried out with hexafluoropropene (1) and perfluorovinyl ethers C3F7O-[CF(CF3)CF2O]n-CF=CF2 (2-4, n=0-2) by direct photoexcitation of the olefins to give high yields of addition products 9-12 (81-94%). The reactions were completely regioselective at the oxolane molecule and almost completely regioselective (93-99%) at the double bond of fluoro-olefins; no bis-fluoroalkylated oxolanes were detected. The completely selective introduction of a second fluoroalkyl into position 5 of the oxolane molecule was accomplished by acetone-sensitised photoaddition of 2-fluoroalkylated oxolanes 9, 10 to fluoro-olefins 1 and 2. Byproducts from reactions of the dimethylketyl radical which is formed in the initiation step were isolated and have given some evidence about the reaction mechanism that is discussed.
  • Oxolane was fluoroalkylated by its photoadditions under atmospheric pressure. Monofluoro-alkylations were carried out with hexafluoropropene (1) and perfluorovinyl ethers C3F7O-[CF(CF3)CF2O]n-CF=CF2 (2-4, n=0-2) by direct photoexcitation of the olefins to give high yields of addition products 9-12 (81-94%). The reactions were completely regioselective at the oxolane molecule and almost completely regioselective (93-99%) at the double bond of fluoro-olefins; no bis-fluoroalkylated oxolanes were detected. The completely selective introduction of a second fluoroalkyl into position 5 of the oxolane molecule was accomplished by acetone-sensitised photoaddition of 2-fluoroalkylated oxolanes 9, 10 to fluoro-olefins 1 and 2. Byproducts from reactions of the dimethylketyl radical which is formed in the initiation step were isolated and have given some evidence about the reaction mechanism that is discussed. (en)
Title
  • Radical Additions to Fluoroolefins. Photochemical Mono-Fluoroalkylation and Sequential Bis-Fluoroalkylation of Oxolane.
  • Radical Additions to Fluoroolefins. Photochemical Mono-Fluoroalkylation and Sequential Bis-Fluoroalkylation of Oxolane. (en)
skos:prefLabel
  • Radical Additions to Fluoroolefins. Photochemical Mono-Fluoroalkylation and Sequential Bis-Fluoroalkylation of Oxolane.
  • Radical Additions to Fluoroolefins. Photochemical Mono-Fluoroalkylation and Sequential Bis-Fluoroalkylation of Oxolane. (en)
skos:notation
  • RIV/67985858:_____/96:27020274!RIV/2003/AV0/A27003/N
http://linked.open.../vavai/riv/strany
  • 125;134
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • Z(AV0Z4072921)
http://linked.open...iv/cisloPeriodika
  • 2
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 833996
http://linked.open...ai/riv/idVysledku
  • RIV/67985858:_____/96:27020274
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • radical addition; regioselectivity; perfluoroolefins (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • NL - Nizozemsko
http://linked.open...ontrolniKodProRIV
  • [343C3EC2D381]
http://linked.open...i/riv/nazevZdroje
  • Journal of Fluorine Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...ocetUcastnikuAkce
http://linked.open...nichUcastnikuAkce
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 80
http://linked.open...iv/tvurceVysledku
  • Církva, Vladimír
  • Paleta, O.
  • Kvíčala, J.
http://linked.open...n/vavai/riv/zamer
issn
  • 0022-1139
number of pages
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