Functionalization of saturated fluorocarbons with and without light
Photochemical transformation of saturated fluorocarbons into tetrabutylammonium enolates has been improved, and a method employing ketyls as reductants has been developed that accomplishes the same chemistry without light. Enolates have been isolated as enol methyl ethers, from which they can be efficiently regenerated with tetrabutylammonium iodide. In other cases, enolates have been isolated as the corresponding ketone or stable enol. Fluorocarbon LUMO energies correlate with their reactivity and serve as a guide to the choice of ketyl. Use of this chemistry for fluoropolymer surface modification is discussed.
Chen, Xudong,Lemal, David M.
p. 1158 - 1167
(2008/09/19)
Functionalization of saturated fluorocarbons
A method is described for transforming perfluoroalkanes and perfluorocycloalkanes bearing tertiary fluorine into perfluoroenolates, which can be variously derivatized.
Stoyanov, Nikolay S.,Ramchandani, Nita,Lemal, David M.
p. 6549 - 6552
(2007/10/03)
POLYFLUOROCYCLOALKENES. PART XVI . SOME ADDITION REACTIONS OF 1-TRIFLUOROMETHYLNONAFLUOROCYCLOHEX-1-ENE
Reactions with alcohols and base repleaced the vinylic fluorine of 1-trifluoromethylnonafluorocyclohex-1-ene (I) by methoxy and ethoxy groups.Fluorination with cobaltic fluoride gave, from the former, a number of saturated polyfluoro-ethers.Oxidation of the alkoxy-cycloalkenes gave hexafluoroglutaric acid.Cycloalkene I gave with ammonia an imino-enamine, which was hydrolysed by dilute acid to a keto-enamine.I was defluorinated by heated iron to octafluorotoluene.
Carter, Paul A.,Patrick, Colin R.,Tatlow, John Colin
p. 407 - 412
(2007/10/02)
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