Tracer studies on the reductive coupling of 1-Naphthyldiazonium ions

Abstract

When 1-naphthyldiazonium ions containing deuterium at the 2- or 4-positions were coupled by various reducing agents to form 1,1′-azonaphthalene, the original orientations of deuterium relative to nitrogen were preserved in both naphthyl rings of the product. The tracer content in the starting material was also retained in products when diazonium ions with nitrogen-15 at either α- or β-positions were similarly treated.

These observations delimit possible mechanisms.