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Abstract:

In this work we have undertaken the radical-induced addition of 1-iodo-n-perfluorobutane onto electron-rich alkenes, alkenes with electron withdrawing groups, and alkynes in water, initiated photochemically. The lack of hydrogen donor (i.e.: (Me 3Si) 3SiH) in our reaction medium facilitates a Halogen Atom-transfer reaction (HAT), affording the respective perfluorobutylated alkyl and alkenyl halides (iodides) in good yields in water. We have also found that water exerts a relevant solvent effect on the rates of perfluoroalkyl radical additions onto double and triple bonds. The stereoselectivity of the radical addition reaction of alkynes is studied. The novelty of this work relies on the photochemical generation of fluorinated radicals in water, and the Halogen Atom-transfer addition reactions of iodoperfluoroalkanes onto carbon-carbon unsaturated bonds in water induced by light. © 2011 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
Autor:Slodowicz, M.; Barata-Vallejo, S.; Vázquez, A.; Nudelman, N.S.; Postigo, A.
Filiación:Faculty of Science, University of Belgrano-Villanueva, 1324 CP, 1428-Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires-Pabellón II, CP 1428, Buenos Aires, Argentina
Palabras clave:Halogen atom transfer; Perfluoroalkyl-substituted compounds; Radical perfluoroalkylation in water
Año:2012
Volumen:135
Página de inicio:137
Página de fin:143
DOI: http://dx.doi.org/10.1016/j.jfluchem.2011.10.002
Título revista:Journal of Fluorine Chemistry
Título revista abreviado:J. Fluor. Chem.
ISSN:00221139
CODEN:JFLCA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00221139_v135_n_p137_Slodowicz

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Citas:

---------- APA ----------
Slodowicz, M., Barata-Vallejo, S., Vázquez, A., Nudelman, N.S. & Postigo, A. (2012) . Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water. Journal of Fluorine Chemistry, 135, 137-143.
http://dx.doi.org/10.1016/j.jfluchem.2011.10.002
---------- CHICAGO ----------
Slodowicz, M., Barata-Vallejo, S., Vázquez, A., Nudelman, N.S., Postigo, A. "Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water" . Journal of Fluorine Chemistry 135 (2012) : 137-143.
http://dx.doi.org/10.1016/j.jfluchem.2011.10.002
---------- MLA ----------
Slodowicz, M., Barata-Vallejo, S., Vázquez, A., Nudelman, N.S., Postigo, A. "Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water" . Journal of Fluorine Chemistry, vol. 135, 2012, pp. 137-143.
http://dx.doi.org/10.1016/j.jfluchem.2011.10.002
---------- VANCOUVER ----------
Slodowicz, M., Barata-Vallejo, S., Vázquez, A., Nudelman, N.S., Postigo, A. Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water. J. Fluor. Chem. 2012;135:137-143.
http://dx.doi.org/10.1016/j.jfluchem.2011.10.002