Fluoroalkyl ethers, synthesis

Jean-Pierre Begue, Daniele Bonnet-Delpon, and Andrei Kornilov 153 WITTIG OLEFINATION OF PER-FLUOROALKYL CARBOXYLIC ESTERS SYNTHESIS OF 1,1,1-TRIFLUORO-2-ETHOXY-5-PHENYLPENT-2-ENE AND 1 -PERFLUOROALKYL EPOXY ETHERS 1,1,1-TRIFLUORO-2-ETHOXY-2,3-EPOXY-5-PHENYLPENTANE... 

Fluoroalcohol ethers, such as —O—CH2—Rf, or ketals of fluoroalkyl ketones. Their synthesis has been described only recently. 

Synthesis and Characterization of Poly(isobutylene-b-mcthyl vinyl ether) Light-Scattering Studies of Poly(ethylene-co-butylene) Polystyrcne-Moc -poly(2-cinnamoylethyl methacrylate) Adsorption IR Spectroscopic Analysis of Poly(l/f,l/f-fluoroalkyl Ot-fluoroacrylate)... 

During the year 1970, several articles were published by Kim et al. [41-46] about the synthesis and the properties of fluorinated hybrid silicone homopolymers and copolymers. These polymers were obtained by hydrosilylation of a, (D-dienes with chlorohydrogenosilanes, and the obtained bis-chlorosilanes were then hydrolysed into bis-silanols and polymerized or copolycondensed (R = R or R or R or R, Z = alkyl, aUcyl ether, fluoroalkyl, fluoroether, etc.) (cf. Scheme 19). 

The synthesis of fluoroalkyl and chlorofluoroalkyl ethers occurs readily by base-catalyzed nucleophilic addition of alcohols to haloalkenes. An example is the s3mthesis of the alkyl 2,2-dichloro-l,l-difluoroethyl ethers, where R is methyl or 1° or 2° alkyl (equation 9.80). Nucleophilic addition can also occur with alkynes that are activated by the presence of groups such as trifluoromethyl. An example is the addition of methoxide to hexafluoro-2-but)me (87) to produce the methoxy ether with trans trifluoromethyl groups (88, equation 9.81). Note that the orientation of addition to the alkyne is anti, a pattern that is frequently— but not always—observed. ... 

Shavnya A, Sakya SM, Munich ML, Rast B, DeMello KL, Jaynes BH (2005) Efficient fluoride-mediated synthesis of 5-alkyl amino- euid ether-substituted pyrazoles. Tetrahedron Lett 46 6887-6891. For the regioselective synthesis of 1-alkyl-5-fluoroalkyl-3-hydroxypyrazoles, see Hamper BC, Kurtzweil ML, Beck JP (1992) Cyclocondensation of alkylhydrazines and p-substituted acetylenic esters Synthesis of 3-hydroxypyrazoles. J Org Chem 57 5680-5686... 

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