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

2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-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...

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Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (16), p.6362-6366
Main Authors: Efimenko, Nikita I, Tomashenko, Olesya A, Spiridonova, Dar’ya V, Novikov, Mikhail S, Khlebnikov, Alexander F
Format: Article
Language:English
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Summary:2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-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-(1H-tetrazol-1-yl)­acetates. Thiophenols react with 2H-azirine-2-carbonyl azides to afford S-aryl 2-(1H-tetrazol-1-yl)­ethanethioates. The mechanism of the nucleophile-induced rearrangement of 2H-azirine-2-carbonyl azides is discussed on the basis of DFT calculations as well as kinetic and 15N labeling experiments.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02157