Acid-Catalyzed Thermal Decomposition of 1-Aryl-3,3-dialkyltriazenes in the Presence of Nucleophiles

Article abstract of DOI:10.1021/jo00302a018

The acid-catalyzed thermal decompositions of a number of 1-aryl-3,3-dialkyltriazenes (1) in the presence of nucleophiles have been conducted with a view to understanding the underlying mechanisms of these reactions.These reactions parallel the corresponding diazonium ion reactions in that a heterolytic dediazoniation path competes with a homolytic route.The relative proportion of the products arising due to these two competing mechanisms depends upon (a) the electron-transfer efficiency of the nucleophile, (b) the redox potential of the aryl diazonium substrate, and (c) the reaction solvent.