Artículo
Heterogeneous photoinduced homolytic aromatic substitution of electron-rich arenes with perfluoroalkyl groups in water and aqueous media - A radical-ion reaction
Barata Vallejo, Sebastian
; Martín Flesia, Marina Aneley
; Lantaño, Beatriz; Argüello, Juan Elias
; Peñeñory, Alicia Beatriz
; Postigo, Jose Alberto
Fecha de publicación:
01/2013
Editorial:
Wiley VCH Verlag
Revista:
European Journal of Organic Chemistry
ISSN:
1434-193X
e-ISSN:
1099-0690
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The photoinduced electron transfer (PET) substitution reaction of electron-rich aromatic nuclei with perfluoroalkyl Rf groups was carried out in water or aqueous mixtures to render substitution products resulting from replacement of aromatic H atoms with the Rf moiety in good yields (57-88 %). Some mechanistic aspects are discussed, supporting the notion of a PET reaction leading to a classical radical homolytic aromatic substitution (HAS) followed by an electron transfer (ET) and then a proton transfer (PT) sequence. A radical mechanism superimposed on a redox process is proposed to account for product formation. Evidence for the radical cation species (as an initiation event) generated from electron-rich arenes in the presence of perfluoroalkyl halides is provided by the UV/Vis transient spectra obtained by Nanosecond Laser Flash Photolysis techniques. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Archivos asociados
Licencia
Identificadores
Colecciones
Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Barata Vallejo, Sebastian; Martín Flesia, Marina Aneley; Lantaño, Beatriz; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; et al.; Heterogeneous photoinduced homolytic aromatic substitution of electron-rich arenes with perfluoroalkyl groups in water and aqueous media - A radical-ion reaction; Wiley VCH Verlag; European Journal of Organic Chemistry; 5; 1-2013; 998-1008
Compartir
Altmétricas