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Effect of different substituents on the one-pot formation of 3,4,5-substituted furan-2(5H)-ones: a kinetics and mechanism study†
Mehdi Shahraki,Sayyed Mostafa Habibi-Khorassani,Maryam Dehdab
RSC Advances Pub Date : 06/09/2015 00:00:00 , DOI:10.1039/C5RA09717G
Abstract

The kinetics of reactions between benzaldehyde and diethyl acetylenedicarboxylate with para-substituted anilines for the one-pot formation of 3,4,5-substituted furan-2(5H)-ones have been studied spectrally at different temperatures in formic acid. For all substituents at the para position of the aniline ring, the reaction followed second-order kinetics. The partial orders with respect to substituted aniline and diethyl acetylenedicarboxylate were one and one, and the reactions also revealed zero-order kinetics in relation to benzaldehyde. Para-electron donating substituents on the aniline ring increased the rate of reaction. On the basis of experimental data, a three step mechanism has been proposed. Kinetic values (k and Ea) and associated activation parameters (ΔH, ΔG and ΔS) of the reactions were determined.

Graphical abstract: Effect of different substituents on the one-pot formation of 3,4,5-substituted furan-2(5H)-ones: a kinetics and mechanism study
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