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Issue 1, 2020
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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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Article information


Submitted
22 Oct 2019
Accepted
05 Nov 2019
First published
05 Nov 2019

Org. Chem. Front., 2020,7, 10-13
Article type
Research Article

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

S. Voltrová, J. Filgas, P. Slavíček and P. Beier, Org. Chem. Front., 2020, 7, 10
DOI: 10.1039/C9QO01295H

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