INVESTIGADORES
POSTIGO Jose Alberto
artículos
Título:
Heterogeneous Photoinduced Homolytic Aromatic Substitution of Electron-rich Arenes with Perfluoroalkyl Groups in Water and Aqueous Media. A Radical-ion Reaction
Autor/es:
BARATA, SEBASTIAN; MARINA MARTIN FLESIA; BEATRIZ LANTAÑO; JUAN E. ARGUELLO; ALICIA PEÑEÑORY *; AL POSTIGO *
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Lugar: Weinheim-DOI: 10.1002/ejoc.201201271; Año: 2013 vol. 2013 p. 998 - 1008
ISSN:
1434-193X
Resumen:
The photoinduced electron transfer (PET) substitution reaction of electron rich aromatic nuclei with perfluoroalkyl groups was carried out in water or aqueous mixtures to render the substitution products resulting from replacement of aromatic H´s with the Rf moiety. Some mechanistic aspects are discussed, supporting the notion of a PET reaction leading to radical homolytic aromatic substitution (HAS) followed by an electron transfer (ET) and then a proton transfer (PT) sequence. A radical mechanism superimposed with 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 transient spectra obtained by Nanosecond Laser Flash Photolysis techniques