Mechanistic studies on the diazo transfer reaction

•Mechanistic studies on the diazo transfer reaction.•Preparation and spectroscopic characterization of isotopically labeled azides.•15N NMR of labeled amino acids and azides.•Confirmation of the mechanism proposed by Wong for azo transfer.

The mechanism of the diazo transfer reaction which converts amines to azides has been studied with labeled amino acids and labeled imidazole-1-sulfonyl azides. Retention of amine nitrogen in the amine, and transfer of the two terminal nitrogen atoms of the imidazole-1-sulfonyl azide to the product, were unambiguously established.

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