678-65-9Relevant articles and documents
Synthesis of telechelic dienes from fluorinated α,ω-diiodoalkanes. Part I. Divinyl and diallyl derivatives from model I(C2F4)nI compounds
Manseri, A.,Ameduri, B.,Boutevin, B.,Kotora, M.,Hajek, M.,Caporiccio, G.
, p. 151 - 158 (2007/10/02)
The synthesis of five fluorinated non-conjugated dienes from commercially available α,ω-diiodoperfluoroalkanes is described.Preparation of the fluorinated divinyl derivatives H2C=CH(CF2)nCH=CH2 (n = 2, 4, 6) (2,2, 2,4 and 2,6) was effected by ethylenation of these diiodinated compounds in various ways followed by dehydroiodination in ethanolic potassium hydroxide.Allyl diolefines, H2C=CHCH2(CF2)nCH2CH=CH2 (4,4 and 4,6) were produced by the α,ω-bis-telomerization of allyl acetate followed by deiodoacetoxylation in the presence of zinc.The diacetate precursors 3,4 and 3,6 of the respective diallyls 4,4 and 4,6 were obtained rather than diacetate 3,2 because of the eventual decomposition of α,ω-diiodoperfluoroethane by β-scission.These five fluorinated non-conjugated dienes have been characterized by 1H, 13C and 19F NMR spectroscopy. - Keywords:Telechelic dienes; Fluorinated vinyl dienes; Fluorinated allyl dienes; α,ω-Diiodoperfluoroalkanes; NMR spectroscopy
Synthesis of Fluorinated Acetylenes
Baum, Kurt,Bedford, Clifford D.,Hunadi, Ronald J.
, p. 2251 - 2257 (2007/10/02)
New routes to fluorinated acetylenes were developed on the basis of additions of iodofluorocarbons to silylacetylenes.Free radical addition of α,ω-diiodoperfluoroalkanes to (trimethylsilyl)acetylene gave the iodotrimethylsilyl olefins Me3SiIC=CH(CF2)nCH=CISiMe3, which reacted with potassium tert-butoxide or DBU to give the (trimethylsilyl)acetylenes and, with an excess of the base, the free diacetylenes.Perfluoroalkyl iodides similarly gave (perfluoroalkyl)acetylenes.The addition of perfluoroheptyl iodide to phenylacetylene, followed by treatment with potassium tert-butoxide gave 1-phenylperfluorononyne.The peroxide-catalyzed reactionof perfluoroalkyl iodides and bis(trimethylsilyl)acetylene gave 1:1 adducts, RF(Me2SiCH2I)C=CHSiMe3, resulting from intramolecular hydrogen abstraction by the initially formed vinyl radical.However, the thermal reaction of perfluoroalkyl iodides and diiodides with bis(trimethylsilyl)acetylene in the presence of free iodine gave the (trimethylsilyl)acetylenes, which were desilylated with potassium fluoride.A route to diacetylenes was investigated on the basis of addition of perfluoroiodo compounds to ethylene, dehydroiodination, brominations, and eliminations.