Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity

Autores
Riveira, Martín Jorge; la Venia, Agustina; Mischne, Mirta Paulina
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Heterogeneous catalytic hydrogenation of unsaturated 1,2,4-trioxanes derived from β-ionone-type dienones has been investigated. Our studies revealed a versatile reactivity of trioxanic substrates that led to the development of reaction methodology for the selective manipulation of the alkene and peroxide functionalities. Depending on the catalytic system used, divergent reaction pathways can be controlled to afford either the corresponding saturated 1,2,4-trioxanes or furan structures. A mechanistic rationalisation, which accounts for the reductive behaviour of these heterocycles, is proposed.
Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mischne, Mirta Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
1,2,4-TRIOXANES
HETEROGENEOUS CATALYTIC HYDROGENATION
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:11336/131331
Acceder
id CONICETDig_211257310dc3a60c846bfe8d6c20dffd
oai_identifier_str oai:ri.conicet.gov.ar:11336/131331
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivityRiveira, Martín Jorgela Venia, AgustinaMischne, Mirta Paulina1,2,4-TRIOXANESHETEROGENEOUS CATALYTIC HYDROGENATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Heterogeneous catalytic hydrogenation of unsaturated 1,2,4-trioxanes derived from β-ionone-type dienones has been investigated. Our studies revealed a versatile reactivity of trioxanic substrates that led to the development of reaction methodology for the selective manipulation of the alkene and peroxide functionalities. Depending on the catalytic system used, divergent reaction pathways can be controlled to afford either the corresponding saturated 1,2,4-trioxanes or furan structures. A mechanistic rationalisation, which accounts for the reductive behaviour of these heterocycles, is proposed.Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Mischne, Mirta Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaPergamon-Elsevier Science Ltd2010-02info: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/11336/131331Riveira, Martín Jorge; la Venia, Agustina; Mischne, Mirta Paulina; Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 51; 5; 2-2010; 804-8070040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/journal/00404039info:eu-repo/semantics/altIdentifier/doi/doi:10.1016/j.tetlet.2009.11.135info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:51:53Zoai:ri.conicet.gov.ar:11336/131331instacron: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:34982025-09-29 09:51:54.222CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
title Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
spellingShingle Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
Riveira, Martín Jorge
1,2,4-TRIOXANES
HETEROGENEOUS CATALYTIC HYDROGENATION
title_short Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
title_full Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
title_fullStr Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
title_full_unstemmed Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
title_sort Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity
dc.creator.none.fl_str_mv Riveira, Martín Jorge
la Venia, Agustina
Mischne, Mirta Paulina
author Riveira, Martín Jorge
author_facet Riveira, Martín Jorge
la Venia, Agustina
Mischne, Mirta Paulina
author_role author
author2 la Venia, Agustina
Mischne, Mirta Paulina
author2_role author
author
dc.subject.none.fl_str_mv 1,2,4-TRIOXANES
HETEROGENEOUS CATALYTIC HYDROGENATION
topic 1,2,4-TRIOXANES
HETEROGENEOUS CATALYTIC HYDROGENATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Heterogeneous catalytic hydrogenation of unsaturated 1,2,4-trioxanes derived from β-ionone-type dienones has been investigated. Our studies revealed a versatile reactivity of trioxanic substrates that led to the development of reaction methodology for the selective manipulation of the alkene and peroxide functionalities. Depending on the catalytic system used, divergent reaction pathways can be controlled to afford either the corresponding saturated 1,2,4-trioxanes or furan structures. A mechanistic rationalisation, which accounts for the reductive behaviour of these heterocycles, is proposed.
Fil: Riveira, Martín Jorge. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mischne, Mirta Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description Heterogeneous catalytic hydrogenation of unsaturated 1,2,4-trioxanes derived from β-ionone-type dienones has been investigated. Our studies revealed a versatile reactivity of trioxanic substrates that led to the development of reaction methodology for the selective manipulation of the alkene and peroxide functionalities. Depending on the catalytic system used, divergent reaction pathways can be controlled to afford either the corresponding saturated 1,2,4-trioxanes or furan structures. A mechanistic rationalisation, which accounts for the reductive behaviour of these heterocycles, is proposed.
publishDate 2010
dc.date.none.fl_str_mv 2010-02
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/11336/131331
Riveira, Martín Jorge; la Venia, Agustina; Mischne, Mirta Paulina; Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 51; 5; 2-2010; 804-807
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/131331
identifier_str_mv Riveira, Martín Jorge; la Venia, Agustina; Mischne, Mirta Paulina; Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 51; 5; 2-2010; 804-807
0040-4039
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/journal/00404039
info:eu-repo/semantics/altIdentifier/doi/doi:10.1016/j.tetlet.2009.11.135
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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_ 1844613593967886336
score 13.070432

Publicaciones similares