Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions

Autores
Crespo Andrada, Karina Fernanda; Peisino, Lucas Ernesto; Güney, Murat; Dastan, Arif; Pierini, Adriana Beatriz
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo–anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn− and Ph2P− anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.
Fil: Crespo Andrada, Karina Fernanda. 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: Peisino, Lucas Ernesto. 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: Güney, Murat. Atatürk University; Turquía
Fil: Dastan, Arif. Atatürk University; Turquía
Fil: Pierini, Adriana 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
Benzonorbornenes
Nucleophilic Substitution
Theoretical Study
Synthetic Scope
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:11336/25010
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactionsCrespo Andrada, Karina FernandaPeisino, Lucas ErnestoGüney, MuratDastan, ArifPierini, Adriana BeatrizBenzonorbornenesNucleophilic SubstitutionTheoretical StudySynthetic Scopehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo–anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn− and Ph2P− anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.Fil: Crespo Andrada, Karina Fernanda. 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: Peisino, Lucas Ernesto. 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: Güney, Murat. Atatürk University; TurquíaFil: Dastan, Arif. Atatürk University; TurquíaFil: Pierini, Adriana 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; ArgentinaRoyal Society of Chemistry2012-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/25010Crespo Andrada, Karina Fernanda; Peisino, Lucas Ernesto; Güney, Murat; Dastan, Arif; Pierini, Adriana Beatriz; Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 6; 12-2012; 955-9651477-0520CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c2ob26768cinfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/C2OB26768C#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:13:49Zoai:ri.conicet.gov.ar:11336/25010instacron: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:34982025-09-10 13:13:49.294CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
title Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
spellingShingle Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
Crespo Andrada, Karina Fernanda
Benzonorbornenes
Nucleophilic Substitution
Theoretical Study
Synthetic Scope
title_short Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
title_full Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
title_fullStr Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
title_full_unstemmed Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
title_sort Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
dc.creator.none.fl_str_mv Crespo Andrada, Karina Fernanda
Peisino, Lucas Ernesto
Güney, Murat
Dastan, Arif
Pierini, Adriana Beatriz
author Crespo Andrada, Karina Fernanda
author_facet Crespo Andrada, Karina Fernanda
Peisino, Lucas Ernesto
Güney, Murat
Dastan, Arif
Pierini, Adriana Beatriz
author_role author
author2 Peisino, Lucas Ernesto
Güney, Murat
Dastan, Arif
Pierini, Adriana Beatriz
author2_role author
author
author
author
dc.subject.none.fl_str_mv Benzonorbornenes
Nucleophilic Substitution
Theoretical Study
Synthetic Scope
topic Benzonorbornenes
Nucleophilic Substitution
Theoretical Study
Synthetic Scope
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 photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo–anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn− and Ph2P− anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.
Fil: Crespo Andrada, Karina Fernanda. 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: Peisino, Lucas Ernesto. 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: Güney, Murat. Atatürk University; Turquía
Fil: Dastan, Arif. Atatürk University; Turquía
Fil: Pierini, Adriana 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 The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo–anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn− and Ph2P− anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.
publishDate 2012
dc.date.none.fl_str_mv 2012-12
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/11336/25010
Crespo Andrada, Karina Fernanda; Peisino, Lucas Ernesto; Güney, Murat; Dastan, Arif; Pierini, Adriana Beatriz; Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 6; 12-2012; 955-965
1477-0520
CONICET Digital
CONICET
url http://hdl.handle.net/11336/25010
identifier_str_mv Crespo Andrada, Karina Fernanda; Peisino, Lucas Ernesto; Güney, Murat; Dastan, Arif; Pierini, Adriana Beatriz; Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 6; 12-2012; 955-965
1477-0520
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c2ob26768c
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/C2OB26768C#!divAbstract
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
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
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score 12.993085

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