Reactions of mesomeric fluorocarbanions with acid anhydrides. Transformation of trifluoromethyl groups into fluorocarbonyl and perfluoroacyl groups

Add time:08/08/2019    Source:sciencedirect.com

It was found that the reaction of mesomeric fluorocarbanions of the CF3CθXCOY type with benzoic anhydride leads to the loss of benzoyl fluoride and the formation of mesomeric carbanions of the FCOCθXCOY type. In a similar reaction with perfluorocarboxylic acid anhydrides, besides a CF3→COF transformation, further change of COF into CORF is observed, leading to the formation of salts containing mesomeric anions of the RFCOCθXCOY type, which, upon acidification, give 1,1- -bis(perfluoroacyl)-2,2,2-trifluoroethanes CF3CH(CORF)2 , tris- (perfluoroacyl)methanes (RFCO)3CH and bis(trifluoroacetyl)- acetic ester (CF3CO)2CHCOOMe. It has been shown that perfluoroalkyl groups in β-diketones and β,β′-triketones may hinder enolization despite their electron-attracting effect.

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