Perfluoro alkyl 1,3-diketonates of cyclic and acyclic secondary amines

Abstract

Cyclic and acyclic secondary amines were quaternized with perfluoroalkyl 1,3-diketones to form secondary ammonium perfluoroalkyl 1,3-diketonates in good yields. Saturated cyclic secondary amines, including morpholine, N-acetylmorpholine, 3-methyl- N-acetylpiperidine, 2,2,6,6-tetramethyl-4-aminopiperidine, 4,4-dimethylimidazoline, 1,3-bispiperidine propane, and acyclic secondary amines, di( n-propyl) amine, di(isopropyl) amine, di( n-butyl) amine, and di(isobutyl) amine were reacted with various fluorine-containing 1,3-diketones ( 1– 5) to yield the corresponding 1,3-diketonates ( 6– 29). The compounds were characterized by 1H, 19F, and 13C NMR, electrospray MS, and elemental analyses. Melting points and T g values were obtained by DSC. Thermal decomposition data (5% weight loss temperature) were recorded by TGA. X-ray single-crystal structures show that 9 and 26 crystallize in monoclinic space group P2(1)/ c.