Abstract
Thermal fragmentation of 3-phenyl-4-aryl-5-phenylimino-1,2,4-oxadiazolines I and II (Ar = Ph, p-tolyl) in a sealed tube under nitrogen gives rise to benzonitrile, arylamines, anilides, phenols, arylureas, and benzimidazole derivatives. In the presence of naphthalene as solvent, I gave alpha- and beta-naphthols beside the previous products. Also, heating of I under reflux in boiling anhydrous tetraline lead to the formation of 1-hydroxytetraline, alpha-tetralone and 1,1'-bitetralyl as the major products. The isolated products have been interpreted in term of a free radical mechanism involving the homolysis of N-O and/or C-N bond.