Thermal decomposition of a Δ³-oxadiazoline

Abstract

<p>2-Methoxy-2,5,5-trimethyl-Δ³-1,3,4-oxadiazoline was synthesized and decomposed neat, in the presence of carbon tetrachloride and in the presence of deuterated benzene. Because of the production of propene when C₆D₆ was the solvent and chlorinated products when CCl₄ was the solvent, a carbene mechanism is proposed. The evidence in support of this mechanism is strengthened by the trapping of the carbene intermediates with 1,1-diphenylethylene and the reaction of independently generated dimethylcarbene with CCl₄.</p>