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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (10), p. 1-6, 2014

DOI: 10.3762/bjoc.10.1

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Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxol-3-one

Journal article published in 2014 by Nico Santschi, Roman C. Sarott ORCID, Elisabeth Otth, Reinhard Kissner, Antonio Togni
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The synthesis of 5-nitro-1-(trifluoromethyl)-3H-1λ3,2-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, 19F 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.