Lithiation of 2-(chloroaryl)-2-aryl-1,3-dioxolanes with butyllithium activated by N,N,N′,N″,N″-pentamethyldiethylenetriamine

Intramolecular competition of variously substituted phenyl rings of benzophenone ketals in lithiation reactions proved to be a useful tool to study both ortho-directing ability and long-range effects of the substituents. The regioselectivities observed in the reaction of benzophenone ketals having one or two chloro substituents in one of the aryl rings with butyllithium complexed to N,N,N′,N″,N″-pentamethyldiethylenetriamine demonstrate the significance of both ortho- and meta-acidifying effect of the chloro substituents. The lithio species thus generated were carboxylated resulting in new polysubstituted benzoic acids.