End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings

Autores
Testero, Sebastian Andres; Mangione, Maria Ines; Suarez, Alejandra Graciela; Spanevello, Rolando Angel
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The end-group-differentiating ozonolysis concept is discussed, with an emphasis on norbornene systems. Different remote functional groups in endo positions in norbornene derivatives are able to direct the primary ozonide fragmentation. By analysis of the factors affecting the regioselectivity, a rule to predict the direction of the primary ozonide rupture is formulated. These reactions give access to highly substituted cyclopentane rings and provide opportunities for their subsequent regioselective manipulation.
Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Materia
Cleavage Reactions
Ozonolysis
Primary Ozonide
Substituent Effects
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:11336/6075
Acceder
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network_name_str CONICET Digital (CONICET)
spelling End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane ringsTestero, Sebastian AndresMangione, Maria InesSuarez, Alejandra GracielaSpanevello, Rolando AngelCleavage ReactionsOzonolysisPrimary OzonideSubstituent Effectshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The end-group-differentiating ozonolysis concept is discussed, with an emphasis on norbornene systems. Different remote functional groups in endo positions in norbornene derivatives are able to direct the primary ozonide fragmentation. By analysis of the factors affecting the regioselectivity, a rule to predict the direction of the primary ozonide rupture is formulated. These reactions give access to highly substituted cyclopentane rings and provide opportunities for their subsequent regioselective manipulation.Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaWiley2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6075Testero, Sebastian Andres; Mangione, Maria Ines; Suarez, Alejandra Graciela; Spanevello, Rolando Angel; End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings; Wiley; European Journal of Organic Chemistry; 2013; 24; 5-2013; 5236-52451434-193Xenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300384/abstractinfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201300384info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:12:30Zoai:ri.conicet.gov.ar:11336/6075instacron: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:34982025-10-22 11:12:31.068CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
title End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
spellingShingle End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
Testero, Sebastian Andres
Cleavage Reactions
Ozonolysis
Primary Ozonide
Substituent Effects
title_short End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
title_full End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
title_fullStr End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
title_full_unstemmed End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
title_sort End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings
dc.creator.none.fl_str_mv Testero, Sebastian Andres
Mangione, Maria Ines
Suarez, Alejandra Graciela
Spanevello, Rolando Angel
author Testero, Sebastian Andres
author_facet Testero, Sebastian Andres
Mangione, Maria Ines
Suarez, Alejandra Graciela
Spanevello, Rolando Angel
author_role author
author2 Mangione, Maria Ines
Suarez, Alejandra Graciela
Spanevello, Rolando Angel
author2_role author
author
author
dc.subject.none.fl_str_mv Cleavage Reactions
Ozonolysis
Primary Ozonide
Substituent Effects
topic Cleavage Reactions
Ozonolysis
Primary Ozonide
Substituent Effects
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 end-group-differentiating ozonolysis concept is discussed, with an emphasis on norbornene systems. Different remote functional groups in endo positions in norbornene derivatives are able to direct the primary ozonide fragmentation. By analysis of the factors affecting the regioselectivity, a rule to predict the direction of the primary ozonide rupture is formulated. These reactions give access to highly substituted cyclopentane rings and provide opportunities for their subsequent regioselective manipulation.
Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Suarez, Alejandra Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
description The end-group-differentiating ozonolysis concept is discussed, with an emphasis on norbornene systems. Different remote functional groups in endo positions in norbornene derivatives are able to direct the primary ozonide fragmentation. By analysis of the factors affecting the regioselectivity, a rule to predict the direction of the primary ozonide rupture is formulated. These reactions give access to highly substituted cyclopentane rings and provide opportunities for their subsequent regioselective manipulation.
publishDate 2013
dc.date.none.fl_str_mv 2013-05
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/11336/6075
Testero, Sebastian Andres; Mangione, Maria Ines; Suarez, Alejandra Graciela; Spanevello, Rolando Angel; End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings; Wiley; European Journal of Organic Chemistry; 2013; 24; 5-2013; 5236-5245
1434-193X
url http://hdl.handle.net/11336/6075
identifier_str_mv Testero, Sebastian Andres; Mangione, Maria Ines; Suarez, Alejandra Graciela; Spanevello, Rolando Angel; End-group differentiating ozonolysis of norbornene systems to access to highly substituted cyclopentane rings; Wiley; European Journal of Organic Chemistry; 2013; 24; 5-2013; 5236-5245
1434-193X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300384/abstract
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201300384
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 Wiley
publisher.none.fl_str_mv Wiley
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 12.982451

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