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

0519343 - ÚOCHB 2021 RIV GB eng J - Journal Article
Voltrová, Svatava - Filgas, Josef - Slavíček, P. - Beier, Petr
Azidofluoromethane: synthesis, stability and reactivity in [3 + 2] cycloadditions.
Organic Chemistry Frontiers. Roč. 7, č. 1 (2020), s. 10-13. ISSN 2052-4129. E-ISSN 2052-4129
R&D Projects: GA MŠMT LTAUSA18037
Institutional support: RVO:61388963
Keywords : thermal decomposition * monofluoromethylation * nucleophiles
OECD category: Organic chemistry
Impact factor: 5.281, year: 2020
Method of publishing: Limited access
https://pubs.rsc.org/en/content/articlelanding/2020/QO/C9QO01295H#!divAbstract

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 beta-ketoesters to furnish 1-fluoromethyl-1,2,3-triazoles.
Permanent Link: http://hdl.handle.net/11104/0304522