Retrograde Aldol Reaction of 3-(1-Hydroxy-2,2,2-trichloroethyl)-2,4-pentanedione Catalyzed by the Bivalent Metal Complexes of 2,4-Pentanedione

doi:10.1246/BCSJ.49.2817

Paper

Retrograde Aldol Reaction of 3-(1-Hydroxy-2,2,2-trichloroethyl)-2,4-pentanedione Catalyzed by the Bivalent Metal Complexes of 2,4-Pentanedione

Published Oct 1, 1976 · K. Uehara, Y. Ohashi, Makoto Tanaka

Bulletin of the Chemical Society of Japan

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Abstract

The bivalent metal complexes of 2,4-pentanedione(M(acac)2) catalyzes the conversion of 3-(1-hydroxy-2,2,2-trichloroethyl)-2,4-pentanedione(A) into chloral and acetylacetone(Hacac) in a chloroform solution. The order of activity of M(acac)2 as the catalyst is: Mg(II), Mn(II)>Co(II)>Ni(II)>Cu(II)<Zn(II). It was found that the catalyzed reaction proceeds through saturation-type kinetics. The Lineweaver-Burk-type plots show linear relationships and are consistent with a mechanism in which a preequilibrium complex formation between M(acac)2 and a substrate is followed by the rate-determining decomposition to give the products. Acetylacetone acts as a competitive inhibitor for the Cu(acac)2-catalyzed reaction. The third stability constant for the Cu–Hacac chelate system can be evaluated from the inhibitor constant as log K3=4.3. The retrograde aldol reactions of 3-(1-hydroxy-2,2,2-trichloroethyl)-5-methyl-2,4-hexanedione and 3-(1-hydroxy-2,2,2-trichloroethyl)-4-phenyl-2,4-butanedione were studied in the same ma...

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Bivalent metal complexes of 2,4-pentanedione catalyze the retrograde aldol reaction of 3-(1-hydroxy-2,2,2-trichloroethyl)-2,4-pentanedione into chloral and acetylacetone in

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Retrograde Aldol Reaction of 3-(1-Hydroxy-2,2,2-trichloroethyl)-2,4-pentanedione Catalyzed by the Bivalent Metal Complexes of 2,4-Pentanedione

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References

The Metal-Ion-Catalyzed Alcoholysis of β-Dicarbonyl Compounds

Metal-ion-catalyzed alcoholysis of -dicarbonyl compounds can efficiently produce,-unsaturated ketones and esters, with a convenient method for alkenyl-substituted compounds in the presence of zinc acetate.

The kinetics of the oxidative polymerization of 2.6-xylenol with a copper-amine complex

Oxidative polymerization of 2.6-xylenol with a copper-amine complex follows a MICHAELIS-MENTEN-type reaction, with oxygen playing a role in catalyst recycling and promoting catalytic action through coordination to intermediate complexes.

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