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 t...

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Autores principales: Santschi, Nico, Sarott, Roman C, Otth, Elisabeth, Kissner, Reinhard, Togni, Antonio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896278/
https://www.ncbi.nlm.nih.gov/pubmed/24454557
http://dx.doi.org/10.3762/bjoc.10.1
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author Santschi, Nico
Sarott, Roman C
Otth, Elisabeth
Kissner, Reinhard
Togni, Antonio
author_facet Santschi, Nico
Sarott, Roman C
Otth, Elisabeth
Kissner, Reinhard
Togni, Antonio
author_sort Santschi, Nico
collection PubMed
description 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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spelling pubmed-38962782014-01-21 Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one Santschi, Nico Sarott, Roman C Otth, Elisabeth Kissner, Reinhard Togni, Antonio Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2014-01-02 /pmc/articles/PMC3896278/ /pubmed/24454557 http://dx.doi.org/10.3762/bjoc.10.1 Text en Copyright © 2014, Santschi et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Santschi, Nico
Sarott, Roman C
Otth, Elisabeth
Kissner, Reinhard
Togni, Antonio
Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
title Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
title_full Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
title_fullStr Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
title_full_unstemmed Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
title_short Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one
title_sort synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3h-1λ(3),2-benziodaoxol-3-one
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896278/
https://www.ncbi.nlm.nih.gov/pubmed/24454557
http://dx.doi.org/10.3762/bjoc.10.1
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