Mononuclear heterocyclic rearrangements. Part 14. Rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazole to 2-aryl-4-phenacyl-1,2,3-triazoles in dioxane–water

Abstract

The kinetics of the title reaction have been measured at various pS⁺ values. The results show the occurrence of general base catalysis and furnish information about substituent effects on the studied reaction. A reaction mechanism analogous to that proposed for the rearrangement of the arylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole is suggested. The reactivity of isoxazole derivatives is much lower than that of 1,2,4-oxadiazole derivatives.