The kinetics of methoxydechlorination of 5-chloro-1,10-phenanthroline and some related reactions

Abstract

The methoxydechlorination of 5-chloro-1,10-phenanthroline occurs readily in DMSO–MeOH (89.9–10.1 w/w) at ca. 60 °C and is without significant side reactions. The dependence of the reaction rate on the concentration of methoxide ions has been determined at several temperatures and the rate has been shown to accord with that expected on the addition–elimination mechanism. Under similar conditions, mono and di-alkylated derivatives are deactivated by addition of methoxide ion to the 2-position, and undergo no methoxydechlorination.