- AMINE-CONTAINING CYCLIC HYDROFLUOROETHERS AND METHODS OF USING THE SAME
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Described herein is a cyclic fluorinated compound of formula (I) where: L is O, CH2, or a covalent bond; X is selected from F or CF3, and Y is selected from H, F, or CF3, wherein when X is CF3 then Y is F and when Y is CF3 then X is F? each Rf1 is independently selected from a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof; or the two Rf1 groups are bonded together to form a fluorinated ring structure comprising 4-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof; the -CFZ-CHAQ group is bonded to a ring carbon that is alpha to at least one O atom of the ring; A is selected from F, or CF3; Z is selected from H, F, or CF3; and Q is selected from (i) a F atom, (ii) a Cl atom, (iii) a linear, cyclic, or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof, or (iv) a G(Rf2)e group, where G is an O atom or a N atom wherein: when Q is a Cl atom, then Z and A are F atoms; when G is O then e is 1, Z is H, F, or CF3; A is F; and Rf2 is a linear or branched perfluorinated alkyl group comprising 1-10 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof; when G is N then e is 2, and each Rf2 group is independently a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof or the two Rf2 groups are bonded together to form a fluorinated ring structure comprising 4-8 carbon atoms and optionally comprising at least one catenated atom selected from O, N, or combinations thereof, with the proviso that when A is CF3 then Z is F, and when Z is CF3 then A is F.
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Paragraph 00118
(2017/09/27)
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- Radical additions to fluoro-olefins. Photochemical mono-fluoroalkylation and sequential bis-fluoroalkylation of oxolane
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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 oleflns 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.
- Paleta, Oldrich,Cirkva, Vladimir,Kvicala, Jaroslav
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p. 125 - 134
(2007/10/03)
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- Free Radical Chemistry. Part 4. Stereoelectronic Effects in the Additions of Cyclic Ethers to Fluorinated Alkenes
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Free-radical additions of cyclic ethers to various fluorinated alkenes have been studied and a clear stereoelectronic effect has been established.The order of reactivity is oxolane > oxepane > oxane and increasing substitution at the double bond leads to lower reactivity of the fluorinated alkene with oxolane.
- Chambers, Richard D.,Grievson, Brian
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p. 2215 - 2218
(2007/10/02)
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