Thermolysis of 2-Diphenylmethylenehydrazono-5, 5-Dimethyl-Δ^3-1,3,4-Oxadiazoline

Abstract

<p> The thermolysis of 2-diphenylmethylenehydrazono-5,5-dimethyl-Δ^3-1,3,4-oxadiazoline in vacuum and in chlorobenzene was studied. In both cases a stable 1-(diphenylmethylene)-4, 4-dimethyl-3-oxo-1,2-diazetidinium inner salt was obtained as the major product. The corresponding imino-oxirane, an isomer of the diazetidinium inner salt, is believed to be a precursor of the above product. Thermolysis of the same oxadiazoline in methanol gave benzophenone methyl carbazate and methyl isopropyl ether, probably involving the initial formation of an isocyanate as an intermediate.</p>