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Information @ a Glance

General

  • Carbonyl compounds are molecules containing the carbonyl group, C=O. These include aldehydes and ketones.

  • Common names are also used for carbonyl-containing substituent groups, which are known collectively as acyl groups.

  • The acidity of β-dicarbonyl compounds is considerably higher than that of monocarbonyl compounds and other dicarbonyl compounds.

  • In keto-enol equilibrium of β-dicarbonyl compounds, the (mono)enolic form usually exceeds the keto form. 2,4-Pentadione, for instance, consists of about 76 percent enolic form.

  • A β-dicarbonyl compound's enol is additionally stabilized through resonance of the enol's carbon-carbon double bond with the second carbonyl group, the enol's hydroxy hydrogen is, on the other hand, connected to the carbonyl oxygen by a hydrogen bridge bond.

Reaction & Synthesis

  • Direct substitution of α-hydrogen of β-dicarbonyl compounds into a fluorine atom is a most efficient method for the synthesis of α-fluoro-β-dicarbonyl compounds which have been used as building blocks for the preparation of biologically active compounds containing a fluorine atom.

  • A novel reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with lactones is described which, depending on the structure of the lactone, affords benzodioxepinones, benzodioxecinones or benzofurans.

  • A reaction did take place, however, when a b-lactone and a cyclic 2-diazo-1,3-dicarbonyl compound  were stirred in the presence of rhodium acetate, the product unexpectedly being the dioxepinone.

  • Compounds such as rhodium acetate and copper acetylacetonate catalyse the reaction, their use being characterised by an induction period which is significantly reduced if a diazo compound is included in the reaction mixture.

Report

  • The difference in O/N-selectivity observed between the L-proline- and L-prolinamide-catalyzed reaction is thought to result from activation of the oxygen through protonation of the nitrogen of nitrosobenzene by the carboxylic acid function of L-proline.

  • The catalytic, enantioselective amination of α-cyanoacetates and β-dicarbonyl compounds with β-isocupreidine (β-ICD 11) to form tetrasubstituted stereocenters.

  • Azodicarboxylates can also serve as electrophiles for the α-amination reaction of 1,3-dicarbonyl compounds via metalloenolates.

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