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