Ketene acetals from thermolysis of aryloxy methoxy oxadiazolines. Evidence for carbonyl ylide intermediates

…, M El-Saidi, J Warkentin

Index: Couture, Philippe; El-Saidi, Manal; Warkentin, John Canadian Journal of Chemistry, 1997 , vol. 75, # 3 p. 326 - 332

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Citation Number: 18

Abstract

Thermolysis of oxadiazolines (5) in benzene at 110° C leads to ketene acetals (11) as minor products. Carbonyl ylide intermediates (6), and oxiranes (7), presumably in equilibrium with those ylides, are implicated as unstable precursors of the ketene acetals although none of the oxiranes (carbonyl protected α-lactones) were isolable and only one of the ketene acetals was isolable in pure form. The evidence points to the two-step sequence of ...