Kinetics of anilinodechlorination of 3-bromo- and 3-methoxy-2-thenoyl chlorides in benzene

Abstract

The susceptibility constants measured for the reaction of 3-bromo-(Ia) and 3-methoxy-2-thenoyl (Ic) chlorides with some meta- and para-substituted anilines in benzene at 25°C have confirmed the occurrence of two different mechanisms for the anilinodechlorination of 3-substituted 2-thenoyl chlorides: (i) the classical AE mechanism and (ii) the IP mechanism (unusual for reactions with anilines in nonpolar aprotic solvents) which can operate when electron-releasing substituents are present in the thiophen ring.