Cleavage of Alkyl-Perfluoroalkyl ethers
Does anyone know conditions under which a perfluoroalkyl-alkyl ether can be cleaved? I recently came across an old can of "outdated" degreaser spray
composed of methyl perfluorobutyl ether and methyl perfluoroisobutyl ether in 1,1-dichloro-1-fluoroethane solvent. The propellant is
1,1,1-2-tetrafluoroethane. Apart from recovering the "solvent" here, I am interested in reactions of the ethers. If they can be cleaved, they should
eliminate HF and form perfluorobutyric and perfluoroisobutyric acid. These acids have pKas of roughly 0, as far as I can tell and might be an
interesting reagent to play around with in lieu of trifluoroacetic acid.
While classic ether cleavage is fairly straightforward, I'd expect the perfluoroalkyl group to have a significant effect on reactivity. I have some
teflon beakers and FEP bottles that could be used as reaction vessels, but condensing a refluxing mix would be impossible (the ethers boil at about
60C presenting a possible problem immediately). Thanks for any help that you can offer.
-UC
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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