Azido-l,2,3-triazolide ion

The scope of the rearrangement reaction whereby azido-l,2,3-triazolide ion (66) is converted to the (diazomethyl)tetrazolide ion (68) has been studied. Where R = H, substituted phenyl, Me, and C02Me the reaction proceeds at a rate which is largely independent of substituent extensive decomposition is observed where R = COMe, COAr, and CN. PM3 calculations used to explore the energy profile of the reaction pathway indicate that the order of anion stability is (67) < (66) < (68) and that the rearrangement is of the type (66) (67) (68) for which 2 and k i ki. 

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