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Reactions of ketenes XVII. Intermediates in the reactions between ketone acetals and ethyl azidoformate

1976; Wiley; Volume: 13; Issue: 2 Linguagem: Inglês

10.1002/jhet.5570130203

1943-5193

M. L. Graziano, R. SCARPATI,

Fluorine in Organic Chemistry

Abstract The reaction of the ketene acetals with ethyl azidoformate proceeds via I‐ethoxycarbonyl‐5,5‐dialkoxy‐Δ 2 ‐1,2,3‐triazolines. The latter decomposes easily at room temperature, the reaction pathway depending on the presence of the substituents at the 4‐position. Thermolysis and photolysis of the 4‐alkyl‐substituted triazolines proceed via 1,3‐diradicals. The photodecomposition of the 4‐unsubstituted triazolines proceeds similarly. The thermal decomposition of the latter is considered either to involve homolytic cleavage of the N 1 N 2 bond to give a 1,5‐diradical, or to proceed by a concerted mechanism.