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

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.