Carbonyl compounds are molecules containing the carbonyl group, C=O.
These include aldehydes and ketones.
names are also used for carbonyl-containing substituent groups, which
are known collectively as acyl groups.
acidity of β-dicarbonyl compounds is considerably higher than that of
monocarbonyl compounds and other dicarbonyl compounds.
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.
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
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
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.
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
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.
catalytic, enantioselective amination of α-cyanoacetates and
β-dicarbonyl compounds with β-isocupreidine (β-ICD 11) to form
Azodicarboxylates can also serve as electrophiles for the α-amination
reaction of 1,3-dicarbonyl compounds via metalloenolates.
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