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Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane
- 1.0577554 - ÚOCHB 2024 RIV US eng J - Journal Article
Shaitanova, Elena - Matoušek, V. - Herentin, T. - Adamec, M. - Matyáš, R. - Klepetářová, Blanka - Beier, Petr
Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane.
Journal of Organic Chemistry. Roč. 88, č. 21 (2023), s. 14969-14977. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR(CZ) GA23-04659S
Institutional support: RVO:61388963
Keywords : tetrafluoroethylene * generation * tetrazoles
OECD category: Organic chemistry
Impact factor: 3.6, year: 2022
Method of publishing: Open access
https://doi.org/10.1021/acs.joc.3c01346
A new fluorinated azidoethane─1-azido-1,1,2,2-tetrafluoroethane─was prepared in quantitative yield by the addition of an azide anion to tetrafluoroethylene in a protic medium. The title azide was shown to be thermally stable and insensitive to impact. Copper(I)-catalyzed [3 + 2] cycloaddition with alkynes afforded 4-substituted N-tetrafluoroethyl-1,2,3-triazoles which underwent rhodium(II)-catalyzed transannulation with nitriles to novel N-tetrafluoroethylimidazoles or the reaction with triflic acid to enamido triflates. [3 + 2] Cycloaddition of the title azide with primary amines afforded novel 5-difluoromethyl tetrazoles.
Permanent Link: https://hdl.handle.net/11104/0346671
Number of the records: 1