Issue 1, 2020

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
22 Oct 2019
Accepted
05 Nov 2019
First published
05 Nov 2019

Org. Chem. Front., 2020,7, 10-13

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements