Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams

Autores
Castro Godoy, Willber David; Oksdath Mansilla, Gabriela; Argüello, Juan Elias; Peñeñory, Alicia Beatriz
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of annulated products. The presence of molecular oxygen changes product distribution, and only photo-oxygenation products (sulfoxides and sulfones) were found. This result is especially valuable since, by simple changing from nitrogen- to oxygen-saturated solvent conditions, the reaction outcome can be tuned from cyclized to sulfur oxidation products. Additionally, steady-state photolysis, electrochemistry, and laser time-resolved spectroscopic studies confirmed that these reactions mainly proceeded by intramolecular electron transfer (ET) between the triplet excited saccharin moiety and sulfur atom.
Fil: Castro Godoy, Willber David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Oksdath Mansilla, Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
HETEROCYCLE
SACCHARIN
CYCLIZATION
PHOTOINDUCED ELECTRON TRANSFER
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:11336/43440
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/43440
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic SultamsCastro Godoy, Willber DavidOksdath Mansilla, GabrielaArgüello, Juan EliasPeñeñory, Alicia BeatrizHETEROCYCLESACCHARINCYCLIZATIONPHOTOINDUCED ELECTRON TRANSFERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of annulated products. The presence of molecular oxygen changes product distribution, and only photo-oxygenation products (sulfoxides and sulfones) were found. This result is especially valuable since, by simple changing from nitrogen- to oxygen-saturated solvent conditions, the reaction outcome can be tuned from cyclized to sulfur oxidation products. Additionally, steady-state photolysis, electrochemistry, and laser time-resolved spectroscopic studies confirmed that these reactions mainly proceeded by intramolecular electron transfer (ET) between the triplet excited saccharin moiety and sulfur atom.Fil: Castro Godoy, Willber David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Oksdath Mansilla, Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaAmerican Chemical Society2016-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/43440Castro Godoy, Willber David; Oksdath Mansilla, Gabriela; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams; American Chemical Society; Journal of Organic Chemistry; 82; 1; 12-2016; 101-1080022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.6b02171info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b02171info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:08:37Zoai:ri.conicet.gov.ar:11336/43440instacron: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:34982025-09-03 10:08:38.003CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
title Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
spellingShingle Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
Castro Godoy, Willber David
HETEROCYCLE
SACCHARIN
CYCLIZATION
PHOTOINDUCED ELECTRON TRANSFER
title_short Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
title_full Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
title_fullStr Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
title_full_unstemmed Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
title_sort Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
dc.creator.none.fl_str_mv Castro Godoy, Willber David
Oksdath Mansilla, Gabriela
Argüello, Juan Elias
Peñeñory, Alicia Beatriz
author Castro Godoy, Willber David
author_facet Castro Godoy, Willber David
Oksdath Mansilla, Gabriela
Argüello, Juan Elias
Peñeñory, Alicia Beatriz
author_role author
author2 Oksdath Mansilla, Gabriela
Argüello, Juan Elias
Peñeñory, Alicia Beatriz
author2_role author
author
author
dc.subject.none.fl_str_mv HETEROCYCLE
SACCHARIN
CYCLIZATION
PHOTOINDUCED ELECTRON TRANSFER
topic HETEROCYCLE
SACCHARIN
CYCLIZATION
PHOTOINDUCED ELECTRON TRANSFER
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of annulated products. The presence of molecular oxygen changes product distribution, and only photo-oxygenation products (sulfoxides and sulfones) were found. This result is especially valuable since, by simple changing from nitrogen- to oxygen-saturated solvent conditions, the reaction outcome can be tuned from cyclized to sulfur oxidation products. Additionally, steady-state photolysis, electrochemistry, and laser time-resolved spectroscopic studies confirmed that these reactions mainly proceeded by intramolecular electron transfer (ET) between the triplet excited saccharin moiety and sulfur atom.
Fil: Castro Godoy, Willber David. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Oksdath Mansilla, Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of annulated products. The presence of molecular oxygen changes product distribution, and only photo-oxygenation products (sulfoxides and sulfones) were found. This result is especially valuable since, by simple changing from nitrogen- to oxygen-saturated solvent conditions, the reaction outcome can be tuned from cyclized to sulfur oxidation products. Additionally, steady-state photolysis, electrochemistry, and laser time-resolved spectroscopic studies confirmed that these reactions mainly proceeded by intramolecular electron transfer (ET) between the triplet excited saccharin moiety and sulfur atom.
publishDate 2016
dc.date.none.fl_str_mv 2016-12
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/11336/43440
Castro Godoy, Willber David; Oksdath Mansilla, Gabriela; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams; American Chemical Society; Journal of Organic Chemistry; 82; 1; 12-2016; 101-108
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/43440
identifier_str_mv Castro Godoy, Willber David; Oksdath Mansilla, Gabriela; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams; American Chemical Society; Journal of Organic Chemistry; 82; 1; 12-2016; 101-108
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.6b02171
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b02171
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
application/pdf
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
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score 13.13397

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