Collect. Czech. Chem. Commun. 1986, 51, 2786-2797

Cyclization and acid-catalyzed hydrolysis of O-benzoylbenzamidoximes

František Grambal and Jan Lasovský

Department of Inorganic and Physical Chemistry, Faculty of Natural Sciences, Palacký University, 772 00 Olomouc


Kinetics of formation of 1,2,4-oxadiazoles from 24 substitution derivatives of O-benzoylbenzamidoxime have been studied in sulphuric acid and aqueous ethanol media. It has been found that this medium requires introduction of the Hammett H0 function instead of the pH scale beginning as low as from 0.1% solutions of mineral acids. Effects of the acid concentration, ionic strength, and temperature on the reaction rate and on the kinetic isotope effect have been followed. From these dependences and from polar effects of substituents it was concluded that along with the cyclization to 1,2,4-oxadiazoles there proceeds hydrolysis to benzamidoxime and benzoic acid. The reaction is thermodynamically controlled by the acid-base equilibrium of the O-benzylated benzamidoximes.