131319-28-3Relevant articles and documents
Radical additions to fluoro-olefins. Photochemical mono-fluoroalkylation and sequential bis-fluoroalkylation of oxolane
Paleta, Oldrich,Cirkva, Vladimir,Kvicala, Jaroslav
, p. 125 - 134 (1996)
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.