Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one.
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.
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH Zürich), Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Nico
N
Santschi
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH Zürich), Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Roman C
RC
Sarott
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH Zürich), Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Elisabeth
E
Otth
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH Zürich), Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Reinhard
R
Kissner
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH Zürich), Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland.
Antonio
A
Togni
19F NMR kinetics; cyclic voltammetry; differential scanning calorimetry; electrophilic trifluoromethylation; nitration; organo-fluorine