67727-68-8Relevant articles and documents
Formation and reactions of carbanions from α-substituted perfluoroacyl fluorides
Chen, L. S.,Eapen, K. C.
, p. 93 - 100 (2007/10/02)
Aliphatic α-substituted perfluoroacyl fluorides are converted to hindered ketones in low to moderate yields on refluxing in acetonitrile with alkali metal fluorides.Other products identified in hydrolyzed reaction mixtures include perfluoroolefins and monohydroperfluoro compounds.A mechanism involving the formation of a carbanion intermediate is proposed.Evidence for the formation of carbanions has been obtained by carrying out the reaction in the presence of bromine and also in the presence of other substrates.
FLUORO-KETONES. V REACTIONS OF ALKYL AND ARYLLITHIUM COMPOUNDS WITH PERFLUOROALKYLETHER ESTERS
Chen, Loomis S.,Tamborski, Christ
, p. 43 - 54 (2007/10/02)
n-Butyllithium and a variety of aryllithium compounds have been shown to react with a perfluoroalkylether ester (RfORfCO2R) at -78 deg C to produce perfluoroalkylether ketones.In the absence of competing reactions, which may be due to additional reactive groups on the ester, high yields of ketones can be prepared.Steric hindrance adjacent to the carbonyl group has an important effect on rates of reactions.Low reaction temperature (-78 deg C) is an important factor when secondary esters are used.At higher reaction temperatures (> -30 deg C), the secondary esters produce decreased yields of ketone due to the instability of the intermediate lithium salt of the hemiketal which decomposes to an aryl ester and a perfluorinated olefin.
