The geminal diazides ethyl α,α-diazidoacetoacetate and α,α-diazidobenzoylacetate were prepared from the corresponding dibromo precursors by nucleophilic azide displacement. Thermolysis of the diazido compounds led to the formation of 2,5-disubstituted 1,3,4-oxadiazoles in high yield.
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Ogilvie et al. (1987) studied this question.