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Updated: Jul 12, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane
Elena Shaitanova1,2, Václav Matoušek3, Tadeáš Herentin3
1Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo Náměstí, 2, 166 10 Prague 6, Czech Republic.
Abstract:
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.
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