Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
Nico Santschi1, Roman C Sarott1, Elisabeth Otth1
1Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH Zürich), Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Abstract:
The synthesis of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one (3), a hypervalent-iodine-based electrophilic trifluoromethylating reagent, is described. Whereas considerations based on cyclic voltammetry and X-ray structural properties would predict an inferior reactivity when compared to the non-nitrated derivative 2, (19)F NMR kinetic studies showed that this new derivative is almost one order of magnitude more reactive. Furthermore, differential scanning calorimetry measurements indicated that, in addition, it is also safer to handle.
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