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Azidofluoromethane: synthesis, stability and reactivity in [3 + 2] cycloadditions

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Abstract

Azidofluoromethane was prepared for the first time by the nucleophilic displacement of bromofluoromethane with sodium azide. This volatile and unstable compound was isolated by low temperature vacuum distillation with a suitable solvent and fully characterized. Theoretical calculations of its decomposition activation energies and rate constants were performed and the values were compared to those for azidomethane, azidodifluoromethane and azidotrifluoromethane. Azidofluoromethane underwent [3 + 2] cycloadditions with alkynes, 1,3-diones and β-ketoesters to furnish 1-fluoromethyl-1,2,3-triazoles.

Graphical abstract: Azidofluoromethane: synthesis, stability and reactivity in [3 + 2] cycloadditions

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Publication details

The article was received on 22 Oct 2019, accepted on 05 Nov 2019 and first published on 05 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01295H
Org. Chem. Front., 2019, Advance Article

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    Azidofluoromethane: synthesis, stability and reactivity in [3 + 2] cycloadditions

    S. Voltrová, J. Filgas, P. Slavíček and P. Beier, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01295H

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