Varying the electronic properties of a supporting ligand is a common approach for optimizing catalytic behavior in many systems.  Here, two new ketoimines were prepared through the Schiff base condensation of a 1,3-diketone and an amine that easily incorporated electron-withdrawing groups into the ketoimine backbone or at the 2-position of the quinoline pendant.  Ketoimine 1  was prepared through the condensation of 5-methyl-1,1,1-trifluoro-2,4-hexanedione with 8-aminoquinoline with toluene reflux for 21 hours and isolated with column chromatography in 28% yield.  Ketoimine 2  was isolated in 15% yield with column chromatography after toluene reflux for 1 day with 2,4-pentanedione and 2-chloro-8-aminoquinoline.  The ketoimines were characterized with 1H, 13C, and 19F NMR, absorbance spectroscopy, and electrospray ionization time-of-flight high-resolution mass spectrometry.  The compounds were used to prepare aluminum complexes that were characterized with NMR spectroscopy and absorbance spectroscopy.  The aluminum complexes were assessed for their ring opening polymerization efficiency of lactide to poly-lactic acid.

Synthesis of ketoimines with electron-withdrawing substituents for use in aluminum complexes

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.