Nucleophile-Induced Rearrangement of 2-Azirine-2-carbonyl Azides to 2-(1-Tetrazol-1-yl)acetic Acid Derivatives.

2-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. The reaction with primary alcohols and phenols gives alkyl/aryl 2-(1-tetrazol-1-yl)acetates.