Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water

Autores
Postigo, Jose Alberto
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The substitution reaction of aromatic nuclei, such as N,N-dialkylated aromatic amines and methoxysubstituted arenes with perfluoroalkyl Rf groups was acomplished in water by a photoinduced method to yield the substitution products resulting from replacement of aromatic H’s with the Rf moiety in good yields (57-88%). Mechanistic aspects are discussed giving support for a photoinduced electron transfer substitution (PET) reaction. A radical chain mechanism superimposed with a redox process is proposed to account for product formation, as evidenced by the observation of the UV-vis transient spectra of the radical cation species generated from electron-rich aromatic compounds in the presence of perfluoroalkyl halides by Nanosecond Laser Flash Photolysis (NLFP) techniques.
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Materia
HOMOLYTIC AROMATIC SUBSTITUTION
PHOTOINDUCED ELECTRON TRANSFER SUBSTITUTION
RADICAL AROMATIC SUBSTITUTION IN WATER
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/217396
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/217396
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in waterPostigo, Jose AlbertoHOMOLYTIC AROMATIC SUBSTITUTIONPHOTOINDUCED ELECTRON TRANSFER SUBSTITUTIONRADICAL AROMATIC SUBSTITUTION IN WATERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The substitution reaction of aromatic nuclei, such as N,N-dialkylated aromatic amines and methoxysubstituted arenes with perfluoroalkyl Rf groups was acomplished in water by a photoinduced method to yield the substitution products resulting from replacement of aromatic H’s with the Rf moiety in good yields (57-88%). Mechanistic aspects are discussed giving support for a photoinduced electron transfer substitution (PET) reaction. A radical chain mechanism superimposed with a redox process is proposed to account for product formation, as evidenced by the observation of the UV-vis transient spectra of the radical cation species generated from electron-rich aromatic compounds in the presence of perfluoroalkyl halides by Nanosecond Laser Flash Photolysis (NLFP) techniques.Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaResearch Trends2012-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/217396Postigo, Jose Alberto; Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water; Research Trends; Trends in Photochemistry & Photobiology; 14; 12-2012; 93-1100972-4532CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.researchtrends.net/tia/title_issue.asp?id=15&in=0&vn=14&type=3info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:59:36Zoai:ri.conicet.gov.ar:11336/217396instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:59:36.378CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
title Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
spellingShingle Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
Postigo, Jose Alberto
HOMOLYTIC AROMATIC SUBSTITUTION
PHOTOINDUCED ELECTRON TRANSFER SUBSTITUTION
RADICAL AROMATIC SUBSTITUTION IN WATER
title_short Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
title_full Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
title_fullStr Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
title_full_unstemmed Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
title_sort Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water
dc.creator.none.fl_str_mv Postigo, Jose Alberto
author Postigo, Jose Alberto
author_facet Postigo, Jose Alberto
author_role author
dc.subject.none.fl_str_mv HOMOLYTIC AROMATIC SUBSTITUTION
PHOTOINDUCED ELECTRON TRANSFER SUBSTITUTION
RADICAL AROMATIC SUBSTITUTION IN WATER
topic HOMOLYTIC AROMATIC SUBSTITUTION
PHOTOINDUCED ELECTRON TRANSFER SUBSTITUTION
RADICAL AROMATIC SUBSTITUTION IN WATER
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The substitution reaction of aromatic nuclei, such as N,N-dialkylated aromatic amines and methoxysubstituted arenes with perfluoroalkyl Rf groups was acomplished in water by a photoinduced method to yield the substitution products resulting from replacement of aromatic H’s with the Rf moiety in good yields (57-88%). Mechanistic aspects are discussed giving support for a photoinduced electron transfer substitution (PET) reaction. A radical chain mechanism superimposed with a redox process is proposed to account for product formation, as evidenced by the observation of the UV-vis transient spectra of the radical cation species generated from electron-rich aromatic compounds in the presence of perfluoroalkyl halides by Nanosecond Laser Flash Photolysis (NLFP) techniques.
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
description The substitution reaction of aromatic nuclei, such as N,N-dialkylated aromatic amines and methoxysubstituted arenes with perfluoroalkyl Rf groups was acomplished in water by a photoinduced method to yield the substitution products resulting from replacement of aromatic H’s with the Rf moiety in good yields (57-88%). Mechanistic aspects are discussed giving support for a photoinduced electron transfer substitution (PET) reaction. A radical chain mechanism superimposed with a redox process is proposed to account for product formation, as evidenced by the observation of the UV-vis transient spectra of the radical cation species generated from electron-rich aromatic compounds in the presence of perfluoroalkyl halides by Nanosecond Laser Flash Photolysis (NLFP) techniques.
publishDate 2012
dc.date.none.fl_str_mv 2012-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/217396
Postigo, Jose Alberto; Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water; Research Trends; Trends in Photochemistry & Photobiology; 14; 12-2012; 93-110
0972-4532
CONICET Digital
CONICET
url http://hdl.handle.net/11336/217396
identifier_str_mv Postigo, Jose Alberto; Homolytic aromatic radical perfluoroalkyl-group substitution of arenes in water; Research Trends; Trends in Photochemistry & Photobiology; 14; 12-2012; 93-110
0972-4532
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.researchtrends.net/tia/title_issue.asp?id=15&in=0&vn=14&type=3
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Research Trends
publisher.none.fl_str_mv Research Trends
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844613767404453888
score 13.070432

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