A reaction of N-sulfonyl-1,2,3-triazole with boron trifluoride etherate afforded a (Z)-β-ensulfonylamido fluoride instead of the previously erroneously assigned E isomer. The correction of the stereochemistry was based on a ge-1D ROESY NMR experiment and X-ray crystal structure analyses. Application of the reaction to N-fluoroalkyl-1,2,3-triazoles afforded new (Z)-β-enamido fluorides in a stereoselective manner. A mechanism involving coordination of BF3 with the triazole ring and vinyl diazonium and vinyl cation intermediates was proposed.

Department of Organic Chemistry Faculty of Science Charles University Hlavova 2030 8 CZ 128 43 Prague 2 Czech Republic

Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic Flemingovo nám 2 166 10 Prague Czech Republic

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