2:1 Adducts Arising from Reactions between Benzynes and 1,3,4-Oxadiazoles

Abstract

2:1 adducts arise from the reaction of 2,5-diaryl-1,3,4-oxadiazoles and benzynes generated from the hexadehydro-Diels−Alder (HDDA) reaction. Density functional theory computations support a mechanistic manifold that includes a concerted S N Ar process. Additionally, the benzyne trapping reaction of 2,5-dimethyl-1,3,4-oxadiazole affords an unusual acylimine-containing 2:1 adduct, which is the first case in which a dearomatized product has arisen from a HDDA reaction.