Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals

Autores
Uranga, Jorge Gustavo; Santiago, Ana Noemi
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Reactions of 2-bromo-, 2-chloronorbornane, 3-chloronorbornan-2-one and 3-bromocamphor with Me3Sn-, Ph2P- or PhS- ions were studied by an SRN1 mechanism in liquid ammonia or DMSO. The results show that substrates having a carbonyl group facilitate electron transfer reactions, which are impeded in the absence of such a group. However, when the free radical formed is stabilized by conjugation, the coupling reaction decreases, causing a concomitant increase in the reduction product. Theoretical studies explain the observed reactivity on the basis of a mechanism involving reductive cleavage as a function of the π-σ interactions.
Fil: Uranga, Jorge Gustavo. 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: Santiago, Ana Noemi. 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
Electron Transfer
Redox Catalysis
B·Lyp
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:11336/70342
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicalsUranga, Jorge GustavoSantiago, Ana NoemiElectron TransferRedox CatalysisB·Lyphttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Reactions of 2-bromo-, 2-chloronorbornane, 3-chloronorbornan-2-one and 3-bromocamphor with Me3Sn-, Ph2P- or PhS- ions were studied by an SRN1 mechanism in liquid ammonia or DMSO. The results show that substrates having a carbonyl group facilitate electron transfer reactions, which are impeded in the absence of such a group. However, when the free radical formed is stabilized by conjugation, the coupling reaction decreases, causing a concomitant increase in the reduction product. Theoretical studies explain the observed reactivity on the basis of a mechanism involving reductive cleavage as a function of the π-σ interactions.Fil: Uranga, Jorge Gustavo. 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: Santiago, Ana Noemi. 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; ArgentinaRoyal Society of Chemistry2010-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/70342Uranga, Jorge Gustavo; Santiago, Ana Noemi; Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals; Royal Society of Chemistry; New Journal of Chemistry; 34; 9; 9-2010; 2006-20121144-05461369-9261CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2010/NJ/b9nj00503j#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/b9nj00503jinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-12-23T13:14:12Zoai:ri.conicet.gov.ar:11336/70342instacron: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:34982025-12-23 13:14:12.622CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
title Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
spellingShingle Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
Uranga, Jorge Gustavo
Electron Transfer
Redox Catalysis
B·Lyp
title_short Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
title_full Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
title_fullStr Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
title_full_unstemmed Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
title_sort Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals
dc.creator.none.fl_str_mv Uranga, Jorge Gustavo
Santiago, Ana Noemi
author Uranga, Jorge Gustavo
author_facet Uranga, Jorge Gustavo
Santiago, Ana Noemi
author_role author
author2 Santiago, Ana Noemi
author2_role author
dc.subject.none.fl_str_mv Electron Transfer
Redox Catalysis
B·Lyp
topic Electron Transfer
Redox Catalysis
B·Lyp
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Reactions of 2-bromo-, 2-chloronorbornane, 3-chloronorbornan-2-one and 3-bromocamphor with Me3Sn-, Ph2P- or PhS- ions were studied by an SRN1 mechanism in liquid ammonia or DMSO. The results show that substrates having a carbonyl group facilitate electron transfer reactions, which are impeded in the absence of such a group. However, when the free radical formed is stabilized by conjugation, the coupling reaction decreases, causing a concomitant increase in the reduction product. Theoretical studies explain the observed reactivity on the basis of a mechanism involving reductive cleavage as a function of the π-σ interactions.
Fil: Uranga, Jorge Gustavo. 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: Santiago, Ana Noemi. 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 Reactions of 2-bromo-, 2-chloronorbornane, 3-chloronorbornan-2-one and 3-bromocamphor with Me3Sn-, Ph2P- or PhS- ions were studied by an SRN1 mechanism in liquid ammonia or DMSO. The results show that substrates having a carbonyl group facilitate electron transfer reactions, which are impeded in the absence of such a group. However, when the free radical formed is stabilized by conjugation, the coupling reaction decreases, causing a concomitant increase in the reduction product. Theoretical studies explain the observed reactivity on the basis of a mechanism involving reductive cleavage as a function of the π-σ interactions.
publishDate 2010
dc.date.none.fl_str_mv 2010-09
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/11336/70342
Uranga, Jorge Gustavo; Santiago, Ana Noemi; Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals; Royal Society of Chemistry; New Journal of Chemistry; 34; 9; 9-2010; 2006-2012
1144-0546
1369-9261
CONICET Digital
CONICET
url http://hdl.handle.net/11336/70342
identifier_str_mv Uranga, Jorge Gustavo; Santiago, Ana Noemi; Reactions of halonorbornane and oxo-substituted derivatives with different anions by the electron transfer mechanism; redox catalysis in stabilized radicals; Royal Society of Chemistry; New Journal of Chemistry; 34; 9; 9-2010; 2006-2012
1144-0546
1369-9261
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2010/NJ/b9nj00503j#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/b9nj00503j
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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_ 1852334968804474880
score 12.441415

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