Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study

Autores
Bonesi, Sergio Mauricio; Protti, Stefano; Albini, Angelo
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The photochemistry of tris(p-bromophenyl)amine was investigated in a nitrogen- and oxygen-flushed solution under laser flash photolysis conditions. The detected intermediates were the corresponding amine radical cation ("Magic Blue") and the N-phenyl-4a,4b-dihydrocarbazole radical cation that, under an oxygen atmosphere, is converted to the corresponding hydroperoxyl radical. The role of the last species was supported by the smooth co-oxidation of sulfides to sulfoxides. On the other hand, co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides arose from an electron transfer between the photogenerated "Magic Blue" and phosphine that prevented the amine cyclization. In this case, intermediate Ar3POO•+ was found to play a key role in phosphine oxide formation.
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Protti, Stefano. Universita Di Pavia; Italia
Fil: Albini, Angelo. Universita Di Pavia; Italia
Materia
Photochemistry
Sulfides and Phosphines
Co oxidation
Magic Blue
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:11336/88627
Acceder
id CONICETDig_500440f1f88a310a7bc3b92ad966f036
oai_identifier_str oai:ri.conicet.gov.ar:11336/88627
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic StudyBonesi, Sergio MauricioProtti, StefanoAlbini, AngeloPhotochemistrySulfides and PhosphinesCo oxidationMagic Bluehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The photochemistry of tris(p-bromophenyl)amine was investigated in a nitrogen- and oxygen-flushed solution under laser flash photolysis conditions. The detected intermediates were the corresponding amine radical cation ("Magic Blue") and the N-phenyl-4a,4b-dihydrocarbazole radical cation that, under an oxygen atmosphere, is converted to the corresponding hydroperoxyl radical. The role of the last species was supported by the smooth co-oxidation of sulfides to sulfoxides. On the other hand, co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides arose from an electron transfer between the photogenerated "Magic Blue" and phosphine that prevented the amine cyclization. In this case, intermediate Ar3POO•+ was found to play a key role in phosphine oxide formation.Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Protti, Stefano. Universita Di Pavia; ItaliaFil: Albini, Angelo. Universita Di Pavia; ItaliaAmerican Chemical Society2018-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/88627Bonesi, Sergio Mauricio; Protti, Stefano; Albini, Angelo; Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study; American Chemical Society; Journal of Organic Chemistry; 83; 15; 8-2018; 8104-81130022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acs.joc.8b00913info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b00913info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:22:11Zoai:ri.conicet.gov.ar:11336/88627instacron: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:34982025-10-15 14:22:11.554CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
title Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
spellingShingle Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
Bonesi, Sergio Mauricio
Photochemistry
Sulfides and Phosphines
Co oxidation
Magic Blue
title_short Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
title_full Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
title_fullStr Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
title_full_unstemmed Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
title_sort Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study
dc.creator.none.fl_str_mv Bonesi, Sergio Mauricio
Protti, Stefano
Albini, Angelo
author Bonesi, Sergio Mauricio
author_facet Bonesi, Sergio Mauricio
Protti, Stefano
Albini, Angelo
author_role author
author2 Protti, Stefano
Albini, Angelo
author2_role author
author
dc.subject.none.fl_str_mv Photochemistry
Sulfides and Phosphines
Co oxidation
Magic Blue
topic Photochemistry
Sulfides and Phosphines
Co oxidation
Magic Blue
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 photochemistry of tris(p-bromophenyl)amine was investigated in a nitrogen- and oxygen-flushed solution under laser flash photolysis conditions. The detected intermediates were the corresponding amine radical cation ("Magic Blue") and the N-phenyl-4a,4b-dihydrocarbazole radical cation that, under an oxygen atmosphere, is converted to the corresponding hydroperoxyl radical. The role of the last species was supported by the smooth co-oxidation of sulfides to sulfoxides. On the other hand, co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides arose from an electron transfer between the photogenerated "Magic Blue" and phosphine that prevented the amine cyclization. In this case, intermediate Ar3POO•+ was found to play a key role in phosphine oxide formation.
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Protti, Stefano. Universita Di Pavia; Italia
Fil: Albini, Angelo. Universita Di Pavia; Italia
description The photochemistry of tris(p-bromophenyl)amine was investigated in a nitrogen- and oxygen-flushed solution under laser flash photolysis conditions. The detected intermediates were the corresponding amine radical cation ("Magic Blue") and the N-phenyl-4a,4b-dihydrocarbazole radical cation that, under an oxygen atmosphere, is converted to the corresponding hydroperoxyl radical. The role of the last species was supported by the smooth co-oxidation of sulfides to sulfoxides. On the other hand, co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides arose from an electron transfer between the photogenerated "Magic Blue" and phosphine that prevented the amine cyclization. In this case, intermediate Ar3POO•+ was found to play a key role in phosphine oxide formation.
publishDate 2018
dc.date.none.fl_str_mv 2018-08
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/11336/88627
Bonesi, Sergio Mauricio; Protti, Stefano; Albini, Angelo; Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study; American Chemical Society; Journal of Organic Chemistry; 83; 15; 8-2018; 8104-8113
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/88627
identifier_str_mv Bonesi, Sergio Mauricio; Protti, Stefano; Albini, Angelo; Photochemical Co-Oxidation of Sulfides and Phosphines with Tris(p-bromophenyl)amine. A Mechanistic Study; American Chemical Society; Journal of Organic Chemistry; 83; 15; 8-2018; 8104-8113
0022-3263
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://pubs.acs.org/doi/10.1021/acs.joc.8b00913
info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b00913
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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_ 1846082618496385024
score 13.22299

Publicaciones similares