Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies

Autores
Siano, Gastón; Crespi, Stefano; Mella, Mariella; Bonesi, Sergio Mauricio
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Irradiation of a series of p-substituted aryl 10 benzoates under N2 atmosphere in homogeneous and micellar 11 media was investigated by means of steady-state condition and 12 of time-resolved spectroscopy. A notable selectivity in favor of 13 the 2-hydroxybenzophenone derivatives was observed in 14 micellar media. The benzophenone derivatives were the 15 main photoproduct. On the other hand, in homogeneous 16 media (cyclohexane, acetonitrile, and methanol) the observed 17 product distribution was entirely different, viz. substituted 2- 18 hydroxybenzophenones, p-substituted phenols, benzyl and 19 benzoic acid were found. The binding constants in the 20 surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of 21 the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 22 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.
Fil: Siano, Gastón. 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: Crespi, Stefano. Universita Degli Studi Di Pavia; Italia
Fil: Mella, Mariella. Universita Degli Studi Di Pavia; Italia
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. Universita Degli Studi Di Pavia; Italia
Materia
Aryl benzoates
Photochemistry
Miicellar media
Homegeneous media
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:11336/151291
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/151291
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studiesSiano, GastónCrespi, StefanoMella, MariellaBonesi, Sergio MauricioAryl benzoatesPhotochemistryMiicellar mediaHomegeneous mediahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Irradiation of a series of p-substituted aryl 10 benzoates under N2 atmosphere in homogeneous and micellar 11 media was investigated by means of steady-state condition and 12 of time-resolved spectroscopy. A notable selectivity in favor of 13 the 2-hydroxybenzophenone derivatives was observed in 14 micellar media. The benzophenone derivatives were the 15 main photoproduct. On the other hand, in homogeneous 16 media (cyclohexane, acetonitrile, and methanol) the observed 17 product distribution was entirely different, viz. substituted 2- 18 hydroxybenzophenones, p-substituted phenols, benzyl and 19 benzoic acid were found. The binding constants in the 20 surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of 21 the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 22 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.Fil: Siano, Gastón. 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: Crespi, Stefano. Universita Degli Studi Di Pavia; ItaliaFil: Mella, Mariella. Universita Degli Studi Di Pavia; ItaliaFil: 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. Universita Degli Studi Di Pavia; ItaliaAmerican Chemical Society2019-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/151291Siano, Gastón; Crespi, Stefano; Mella, Mariella; Bonesi, Sergio Mauricio; Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies; American Chemical Society; Journal of Organic Chemistry; 84; 7; 3-2019; 4338-43520022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.9b00334info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.9b00334info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:40:18Zoai:ri.conicet.gov.ar:11336/151291instacron: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 15:40:19.243CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
title Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
spellingShingle Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
Siano, Gastón
Aryl benzoates
Photochemistry
Miicellar media
Homegeneous media
title_short Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
title_full Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
title_fullStr Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
title_full_unstemmed Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
title_sort Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
dc.creator.none.fl_str_mv Siano, Gastón
Crespi, Stefano
Mella, Mariella
Bonesi, Sergio Mauricio
author Siano, Gastón
author_facet Siano, Gastón
Crespi, Stefano
Mella, Mariella
Bonesi, Sergio Mauricio
author_role author
author2 Crespi, Stefano
Mella, Mariella
Bonesi, Sergio Mauricio
author2_role author
author
author
dc.subject.none.fl_str_mv Aryl benzoates
Photochemistry
Miicellar media
Homegeneous media
topic Aryl benzoates
Photochemistry
Miicellar media
Homegeneous media
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Irradiation of a series of p-substituted aryl 10 benzoates under N2 atmosphere in homogeneous and micellar 11 media was investigated by means of steady-state condition and 12 of time-resolved spectroscopy. A notable selectivity in favor of 13 the 2-hydroxybenzophenone derivatives was observed in 14 micellar media. The benzophenone derivatives were the 15 main photoproduct. On the other hand, in homogeneous 16 media (cyclohexane, acetonitrile, and methanol) the observed 17 product distribution was entirely different, viz. substituted 2- 18 hydroxybenzophenones, p-substituted phenols, benzyl and 19 benzoic acid were found. The binding constants in the 20 surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of 21 the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 22 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.
Fil: Siano, Gastón. 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: Crespi, Stefano. Universita Degli Studi Di Pavia; Italia
Fil: Mella, Mariella. Universita Degli Studi Di Pavia; Italia
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. Universita Degli Studi Di Pavia; Italia
description Irradiation of a series of p-substituted aryl 10 benzoates under N2 atmosphere in homogeneous and micellar 11 media was investigated by means of steady-state condition and 12 of time-resolved spectroscopy. A notable selectivity in favor of 13 the 2-hydroxybenzophenone derivatives was observed in 14 micellar media. The benzophenone derivatives were the 15 main photoproduct. On the other hand, in homogeneous 16 media (cyclohexane, acetonitrile, and methanol) the observed 17 product distribution was entirely different, viz. substituted 2- 18 hydroxybenzophenones, p-substituted phenols, benzyl and 19 benzoic acid were found. The binding constants in the 20 surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of 21 the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 22 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.
publishDate 2019
dc.date.none.fl_str_mv 2019-03
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/11336/151291
Siano, Gastón; Crespi, Stefano; Mella, Mariella; Bonesi, Sergio Mauricio; Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies; American Chemical Society; Journal of Organic Chemistry; 84; 7; 3-2019; 4338-4352
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/151291
identifier_str_mv Siano, Gastón; Crespi, Stefano; Mella, Mariella; Bonesi, Sergio Mauricio; Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies; American Chemical Society; Journal of Organic Chemistry; 84; 7; 3-2019; 4338-4352
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/doi/10.1021/acs.joc.9b00334
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.9b00334
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_ 1846083517670227968
score 13.22299

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