92604-95-0Relevant academic research and scientific papers
Synthese d'alkyl(perfluoroalcenyl)cetones RH-CO-CF=CF-RF. Competition entre addition et enolisation au cours de la reaction des chlorures d'acyle sur la halogenures de perfluoroalcenyl magnesium (1)
Moureau, Patrice,Redwane, Nehza,Commeyras, Auguste
, p. 117 - 123 (2007/10/02)
Acyl chlorides react with perfluorooctenylmagnesium bromide C6F13-CF=CF-MgBr to give, depending on experimental conditions, the corresponding ketones and (or) tertiary alcohols.Acetyl chloride leads to results similar to those obtained with the hydrocarbon series.In the case of propionyl and isobutyryl chlorides, the formation of the tertiary alcohol takes place only at low temperature, whereas an increase in the temperature leads to the exclusive formation of the ketone RH-CO-CF=CF-C6F13 in high yields.These results may be interpreted in terms of a competition between a normal addition reaction of the Grignard reagent on the acyl chloride and an enolization reaction.The latter, which becomes the main reaction at room temperature, is due to the presence, in α position of the carbonyl group of the intermediate ketone, of an unsaturated perfluorinated chain increasing the electrophilic character of the carbonyl carbon atom.Alkyl(perfluoroalkenyl)ketones RH-CO-CF=CF-RF constitute a hitherto unknown class of ketones.
