Collect. Czech. Chem. Commun. 1981, 46, 506-514

Kinetic and spectral studies on 5-phenoxy-2-furaldehydes and their condensation products

Viera Knoppová, Miloslava Dandárová and Jaroslav Kováč

Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava


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.