Kinetic Studies on Darzens’ Condensation of Chrysenequinone and its Mononitrogenous Derivatives

Year 1981, Volume: 27 , 0 - 0, 01.01.1981

William I. Awad

https://doi.org/10.1501/Commub_0000000129

Abstract

The kinetics of the following Systems were followed potentiometrically, at different tempe- taturesr in alkaline medium; (A) condens of chryseneqiuinone with phenacylychloride and with its p-methoxy, p-methyl and p-chloro derivatives. The condensation follow an overall third order kinetics, first with respect to each constituent.The rate inereases hy inereasing the eleetron withdrawing power of the substituted groups. The rate also inereases as the dielectric constant of the medium increases.(B)condensation of chrysenequinone, chrysenequinoneinrine, and erhy- senequinone monoxime with o-and p-nitrobenzy Ichloeides. The reaction of the imine could not be followed because it was either partially hydrolyzed, or partially immiscible with the solvent. The condensations follow an overall second order kinetics, first with respect to the halogen- methylene compound and the alkali, and independent of the quinone. The rate of the reaction decrease as the dielectric constant of the medium inereases. The rate of condensation of chrys- ene quinone is faster than the monoxime. Also p-nitrobenzyl chloride reacts with chryseneq- uinonemuch faster than the o-derivative.

Keywords

Kinetic Studies, Darzens’ Condensation, Chrysenequinone

References

• Communications Faculty of Sciences University of Ankara Series B Chemistry and Chemical Engineering