Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

The base-catalyzed reaction of 5-(4- or 3-phenoxy)-2-furaldehydes (X = 4-OCH₃, 4-CH₃, 4-Cl, 4-NO₂, 3-NO₂, 4-Br, 4-COOC₂H₅, 3-NHCOCH₃, 4-SCH₃) with malonodinitrile in ethanol gave the corresponding condensation products. The course of the reaction has been monitored kinetically. The kinetics of the nucleophilic substitution reaction at the position 5 of the furan ring of the obtained 2-cyano-3-(5-X-phenoxy-2-furyl)acrylonitriles with secondary cyclic amines (piperidine, morpholine, pyrrolidine) has been studied. The effect of X across the oxygen bridge upon the reaction site is discussed from the point of view of kinetics of the reaction. ¹H-NMR spectra of the starting aldehydes and of the formed condensation products have been measured.