Ring-opening isomerization addition reaction of bicyclo ortho esters with acid chlorides. Model reaction for development of a novel polyaddition reaction accompanying ring-opening isomerization

Abstract

The reaction of bicyclo ortho esters (BOEs) with acid chlorides was examined. The BOEs readily reacted with acid chlorides to give the corresponding adducts via ring-opening isomerization. The order of the reactivities of the acid chlorides is as follows, sebacoyl chloride ⪈ adipoyl chloride > succinyl chloride and 1,3,5-benzenetricarbonyl chloride > isophthaloyl chloride ⪈ benzoyl chloride. It is considered that the ring-opening isomerization of the BOEs with acid chlorides proceeds by a similar mechanism as that of the homopolymerization of the BOEs.