The Mechanism of Aminations of Halobenzenes¹

Abstract

An elimination-addition mechanism, probably involving a "benzyne" intermediate, has been established for the rearrangements which often occur in the conversion of non-activated aryl halides to arylamines with metallic amides. The evidence for the "benzyne" intermediate was obtained through ^(14)C-tracer studies of rearrangements with halobenzenes and experiments designed to determine the role of the hydrogen atom located ortho to the displaced halogen atom.