THE SYNTHESIS AND THERMAL DECOMPOSITION OF 5,5-DIPHENYL-2-(ARYLIMINO)-Δ³-1,3,4-OXADIAZOLINES AND 5,5-DIALKYL-Δ³-1,3,4-OXADIAZOLIN-2-ONES

Abstract

<p>The thermal decomposition of 2-(arylimino)-5,5diphenyl-Δ³-1,3,4-oxadiazolines, prepared by the oxidation of benzophenone 4-arylsemicarbazones by lead tetra-acetate, was studied. A possible mechanism of the decomposition is discussed in the light of a correlation between the rate constants and substituent constants. The configuration of N,5,5-trisubstituted-2-imino-Δ³-1,3,4-oxadiazolines was determined. Several new compounds, 5,5-dialkyl-Δ³-1,3,4-oxadiazolin-2-ones, were prepared by hydrolysis of 5,5-dialkyl-2-(methylimino)-Δ³-1,3,4-oxadiazolines. A literature survey of the oxidative cyclization of nitrogen-containing carbonyl derivatives, and of the thermal decomposition of cyclic azo compounds is presented.</p>