Rearrangement of substituted azido-1,2,3-triazolides to (α-diazoalkyl)tetrazolides

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Lutz Preu, Andreas Beißner and Dietrich Moderhack


Abstract

The scope of the title process has been studied, showing that anions 4′ having R = H, (substituted) Ph and CO2Me react cleanly (and still satisfactorily in the case R = Me), while with R = COMe, COAr and CN extensive decomposition occurs. The experimental findings (rate constants, activation parameters) have been elucidated through PM3 calculations.


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