Mononuclear Rearrangement of the Z‑Phenylhydrazones of Some 3‑Acyl-1,2,4-oxadiazoles: Effect of Substituents on the Nucleophilic Character of the >CN–NH–C6 H5 Chain and on the Charge Density of N‑2 of the 1,2,4-Oxadiazole Ring (Electrophilic Counterpart)

The reaction rates for the mononuclear rearrangement of the Z-phenylhydrazones of 3-acyl-1,2,4-oxadiazoles 3a–c into the relevant 2-phenyl-2H-1,2,3-triazoles (4a–c) have been measured in dioxane/water at different temperatures in a large range of proton concentrations. The occurrence of two different reaction pathways (one uncatalyzed, water assisted, and the other general base catalyzed) has- been observed. The obtained results have been able to furnish information about the effects of the nature of the 3-acyl structure and of the 5-substituents in the 1,2,4-oxadiazole ring on the reactivity of the examined rearrangements: they are well in line with the previsions carried out considering some our previous computational results as well as experimental kinetic ones.