Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives

Pseudocyclic β-trifluorosulfonyloxy vinylbenziodoxolones were prepared starting from hydroxybenziodoxolones and alkynes in the presence of trifluoromethanesulfonic acid. The reaction of these compounds with azide anion leads to β-azido vinylbenziodoxolones as products of vinylic nucleophilic substitution in which addition-elimination reactions occur and the double bond configuration is retained. The structures of β-trifluorosulfonyloxy vinylbenziodoxolone and β-azido vinylbenziodoxolone were established by single crystal X-ray diffraction. (Figure presented.).