Reactions of perfluoroalkylacetones with nucleophilic reagents

Article abstract of DOI:10.1016/S0022-1139(96)03451-3

The interaction of perfluoroalkylacetones of formula R_FCH₂COCH₃ (R_F=n-C₃F₇, n-C₄F₉, n-C₆F₁₃, n-C₈F₁₇) with ammonia and primary and secondary amines has been studied. In all cases, nucleophilic reagents initially dehydrofluorinate the starting ketone, and then substitution of the vinyl fluorine atom by a nucleophile occurs to give aza analogues of β-dicarbonyl compounds R_FC(NR₂)=CH-C(O)CH₃; their hydrolysis yields the corresponding β-diketones under mild conditions. Perfluoroalkylacetones react with sodium alkoxides to give compounds of formula R_FC(OR)₂CH₂COCH₃, whose acidic hydrolysis also results in β-diketones.