(Co)oxidation/cyclization processes upon irradiation of triphenylamine

Autores
Bonesi, Sergio Mauricio; Dondi, Daniele; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Abstract. Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides.
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Dondi, Daniele. Universita Di Pavia; Italia
Fil: Protti, Stefano. Universita Di Pavia; Italia
Fil: Fagnoni, Maurizio. Universita Di Pavia; Italia
Fil: Albini, Angelo. Universita Di Pavia; Italia
Materia
Photooxidation
Photocyclization
Phosphine Oxidation
Sulphide Oxidation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/8155
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling (Co)oxidation/cyclization processes upon irradiation of triphenylamineBonesi, Sergio MauricioDondi, DanieleProtti, StefanoFagnoni, MaurizioAlbini, AngeloPhotooxidationPhotocyclizationPhosphine OxidationSulphide Oxidationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Abstract. Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides.Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Dondi, Daniele. Universita Di Pavia; ItaliaFil: Protti, Stefano. Universita Di Pavia; ItaliaFil: Fagnoni, Maurizio. Universita Di Pavia; ItaliaFil: Albini, Angelo. Universita Di Pavia; ItaliaElsevier2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/8155Bonesi, Sergio Mauricio; Dondi, Daniele; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; (Co)oxidation/cyclization processes upon irradiation of triphenylamine; Elsevier; Tetrahedron Letters; 55; 18; 4-2014; 2932–29350040-4039enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403914005073info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2014.03.086info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:54:17Zoai:ri.conicet.gov.ar:11336/8155instacron: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 14:54:17.371CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv (Co)oxidation/cyclization processes upon irradiation of triphenylamine
title (Co)oxidation/cyclization processes upon irradiation of triphenylamine
spellingShingle (Co)oxidation/cyclization processes upon irradiation of triphenylamine
Bonesi, Sergio Mauricio
Photooxidation
Photocyclization
Phosphine Oxidation
Sulphide Oxidation
title_short (Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_full (Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_fullStr (Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_full_unstemmed (Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_sort (Co)oxidation/cyclization processes upon irradiation of triphenylamine
dc.creator.none.fl_str_mv Bonesi, Sergio Mauricio
Dondi, Daniele
Protti, Stefano
Fagnoni, Maurizio
Albini, Angelo
author Bonesi, Sergio Mauricio
author_facet Bonesi, Sergio Mauricio
Dondi, Daniele
Protti, Stefano
Fagnoni, Maurizio
Albini, Angelo
author_role author
author2 Dondi, Daniele
Protti, Stefano
Fagnoni, Maurizio
Albini, Angelo
author2_role author
author
author
author
dc.subject.none.fl_str_mv Photooxidation
Photocyclization
Phosphine Oxidation
Sulphide Oxidation
topic Photooxidation
Photocyclization
Phosphine Oxidation
Sulphide Oxidation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Abstract. Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides.
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Dondi, Daniele. Universita Di Pavia; Italia
Fil: Protti, Stefano. Universita Di Pavia; Italia
Fil: Fagnoni, Maurizio. Universita Di Pavia; Italia
Fil: Albini, Angelo. Universita Di Pavia; Italia
description Abstract. Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides.
publishDate 2014
dc.date.none.fl_str_mv 2014-04
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/11336/8155
Bonesi, Sergio Mauricio; Dondi, Daniele; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; (Co)oxidation/cyclization processes upon irradiation of triphenylamine; Elsevier; Tetrahedron Letters; 55; 18; 4-2014; 2932–2935
0040-4039
url http://hdl.handle.net/11336/8155
identifier_str_mv Bonesi, Sergio Mauricio; Dondi, Daniele; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; (Co)oxidation/cyclization processes upon irradiation of triphenylamine; Elsevier; Tetrahedron Letters; 55; 18; 4-2014; 2932–2935
0040-4039
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403914005073
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2014.03.086
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
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score 13.22299

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