Reactions of ethyl triphenylphosphoranylideneacetate with fluorinated β-ketoaldehyde derivatives

The reactions of fluorinated β-ketoaldehyde derivatives: β-alkoxyvinyl polyfluoroalkyl ketones 1 and fluorinated β-ketoacetals 2 with ethyl triphenylphosphoranylideneacetate 3 are described. In the case of ketones 1 the result of the reaction is a mixture of products: fluorinated alkoxydienes 5 (Wittig reaction product) and polyfluoroacyl vinyl ylides 7 (Michael addition product). The reaction with fluorinated β-ketoacetals 2 leads to a mixture of E- and Z-isomers of polyfluoroalkyl acrylates 8 and 9, respectively. The influence of the nature of fluorinated substituent and solvent or other factors on the outcome of the reactions are discussed.