Fluoroalkyl allyl ethers: Useful building blocks for the synthesis of environmentally safer fluorinated multiblock molecules

Fluorous ethers

“…Fluorination of dialkyl-ethers and polyethers has been the most used direct synthesis of perfluoroethers such as 1, 4 and 13 with different molecular weights and boiling points (Table 1). 25 A series of fluorous dialkyl-ethers 5-7, 10 and 16 (Table 1) were prepared by using the Mitsunobu reaction of perfluoro and perfluoroalkyl alcohols (Scheme 5). 24 Long-chain containing fluorous ethers 3 and 8 (Table 1) were synthesised by preparing fluorous iodides from fluorous allyl ethers and perfluoroalkyl iodides in the presence of AIBN and aqueous Na 2 S 2 O 5 , followed by the heterogeneous palladium catalysed hydrogenation (Scheme 4).…”

“…The cytotoxicity of these fluorous ethers was shown to be lower than PFOA. 25 Fluorous ethers 50 and 51 are analogues of 6 and 7, and were prepared by the Mitsunobu reaction of the appropriate perfluoro and fluorous alcohols. 24 49 was synthesised by preparing fluorous iodides from perfluoropropyl allyl ether and perfluorobutyl iodide in the presence of AIBN and aqueous Na 2 S 2 O 5 , followed by the heterogeneous palladium catalysed hydrogenation.…”

“…24 Long-chain containing fluorous ethers 3 and 8 (Table 1) were synthesised by preparing fluorous iodides from fluorous allyl ethers and perfluoroalkyl iodides in the presence of AIBN and aqueous Na 2 S 2 O 5 , followed by the heterogeneous palladium catalysed hydrogenation (Scheme 4). 25 A series of fluorous dialkyl-ethers 5-7, 10 and 16 (Table 1) were prepared by using the Mitsunobu reaction of perfluoro and perfluoroalkyl alcohols (Scheme 5). 26 The palladium catalysed reaction of 1H,1H,2H,2H-perfluorooctanol with 4-methyl-2-pentanone under hydrogen has been used for the synthesis of fluorous ether 11 (F-626) (Scheme 6).…”

“…24 49 was synthesised by preparing fluorous iodides from perfluoropropyl allyl ether and perfluorobutyl iodide in the presence of AIBN and aqueous Na 2 S 2 O 5 , followed by the heterogeneous palladium catalysed hydrogenation. 25 Fluorous ethers 50 and 51 are analogues of 6 and 7, and were prepared by the Mitsunobu reaction of the appropriate perfluoro and fluorous alcohols. 26…”

Hydrophobic Materials Based on Fluorocarbofunctional Spherosilicates

“…The main reagents are octakis(hydridodimethylsiloxy)octasilsesquioxane (that is obtained in a simple and fast way based on the method described in the literature [29]) and fluoroalkyl allyl ether. The preparation of the latter reagent is based on the Williamson reaction by using fluorinated alcohols (that are considerably cheaper than commonly used fluoroalkyl iodides) and allyl chloride [30]. In the present study, based on the developed method of consecutive hydrosilylation of different olefins, syntheses were performed of subsequent silsesquioxanes containing, besides fluoroalkyl groups, also trimethoxysilylethyl groups that are susceptible to hydrolysis and condensation and due to this ability they can form covalent bonds with a substrate surface.…”