SYNTHESIS OF FLUORINATED α-DIKETONES AND SOME INTERMEDIATES

Article abstract of DOI:10.1016/S0022-1139(00)82657-3

Reactions of perfluoroalkylcopper compounds with α-ketoacyl chlorides were used for the synthesis of fluorinated α-diketones.Heptafluoropropylcopper prepared from copper bronze and 1-iodoheptafluoropropane reacted with benzoylformyl chloride to give heptafluoro-1-phenyl-1,2-pentanedione, with trimethylpyruvyl chloride to give 2,2-dimethyl-5,5,6,6,7,7,7-heptafluoro-3,4-heptanedione, and with 3,3,4,4,5,5,5-heptafluoro-2-keto-pentanoyl chloride or oxalyl chloride to give tetradecafluoro-4,5-octane-dione.Syntheses of fluorinated acetylenes, cyanohydrins, α-hydroxy acids, α-keto acids, their chlorides, and other intermediates for the syntheses of α-diketones by the above route and by other methods are described.An interesting seven-membered ring containing β-hydroxy ketone was obtained by an intramolecular aldol condensation of a fluorinated bis(methyl) ketone.