D. Sevenard, O. Kazakova, E. Lork
Nov 26, 2007
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Influential Citations
5
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract 4-Phenyl-2,6-bis(trifluoroacetyl)cyclohexanone and its dilithium salt were synthesized starting from the commercially available 4-phenylcyclohexanone. With X-ray structure analysis of these compounds, for the first time the solid state structure determination for a fluorinated 1,3,5-triketone and an alkaline salt of 1,3,5-triketone was achieved. The subsequent multinuclear NMR and MS investigations revealed that in solution and gas phase, analogously to the crystal, both compounds exist predominantly in a highly delocalized double U-enol(ate) form. The carbonyl O…O distances in the dilithium salt were established to be considerably longer than the distances between oxygens of the parent 1,3,5-triketone, bonded by strong (short) resonance assisted hydrogen bonds. Among the 1,3,5-tricarbonyl compounds with known crystal structure, the entitled 1,3,5-triketone shows comparatively weak delocalization over the conjugated bis-enolone backbone.