Organometallic CN coupling between N,N′-dichloro-p-benzoquinone diimine and Grignard reagents and its application to synthesis of polyanilines

A new C–N coupling reaction between N,N′-dichloro-p-benzoquinone diimines and aryl Grignard reagents has been developed. The new method gives N,N′-diaryl-p-benzoquinone diimines in 50–88% isolated yield. The obtained new compounds are regarded as oligomeric model compounds for pernigraniline-type polyaniline, and their chemical behavior has been investigated. New polyaniline-type polymers have been prepared by applying the developed C–N coupling reaction.