Improved synthesis of bis(chloromethyl)arene monomers

Autores
Almassio, Marcela; Sarimbalis, Myrian N.; Garay, Raúl Oscar
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We report here on the experimental conditions for radical chlorination that provide improved yields of 2,5-bis(chloromethyl) pyridine and pyrazine, as well as on theoretical calculations which were performed in order to gain some insight regarding the factors that affect reactivity in these systems. The difficulties encountered previously in the methyl functionalization of N-heteroarenes are not due to radical selectivity that produces low yield of the dichlorides or to lower reactivity of this type of compounds, but to the post-halogenation reactions that occur on the desired products. Therefore, a careful handling during and after the reaction allowed us to find conditions for product optimization of α, α′-dichlorinated monomers.
Fil: Almassio, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Fil: Sarimbalis, Myrian N.. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Fil: Garay, Raúl Oscar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Materia
BIS(HALOMETHYL)ARYL
CONJUGATED POLY-MERS
HALOGENATION
MONOMERS
PRODUCT OPTIMIZATION
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:11336/96981
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Improved synthesis of bis(chloromethyl)arene monomersAlmassio, MarcelaSarimbalis, Myrian N.Garay, Raúl OscarBIS(HALOMETHYL)ARYLCONJUGATED POLY-MERSHALOGENATIONMONOMERSPRODUCT OPTIMIZATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We report here on the experimental conditions for radical chlorination that provide improved yields of 2,5-bis(chloromethyl) pyridine and pyrazine, as well as on theoretical calculations which were performed in order to gain some insight regarding the factors that affect reactivity in these systems. The difficulties encountered previously in the methyl functionalization of N-heteroarenes are not due to radical selectivity that produces low yield of the dichlorides or to lower reactivity of this type of compounds, but to the post-halogenation reactions that occur on the desired products. Therefore, a careful handling during and after the reaction allowed us to find conditions for product optimization of α, α′-dichlorinated monomers.Fil: Almassio, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; ArgentinaFil: Sarimbalis, Myrian N.. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; ArgentinaFil: Garay, Raúl Oscar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; ArgentinaVsp Bv2005-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/96981Almassio, Marcela; Sarimbalis, Myrian N.; Garay, Raúl Oscar; Improved synthesis of bis(chloromethyl)arene monomers; Vsp Bv; Designed Monomers And Polymers; 8; 4; 12-2005; 287-2961385-772XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/abs/10.1163/1568555054460024info:eu-repo/semantics/altIdentifier/doi/10.1163/1568555054460024info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:36:21Zoai:ri.conicet.gov.ar:11336/96981instacron: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 09:36:21.314CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Improved synthesis of bis(chloromethyl)arene monomers
title Improved synthesis of bis(chloromethyl)arene monomers
spellingShingle Improved synthesis of bis(chloromethyl)arene monomers
Almassio, Marcela
BIS(HALOMETHYL)ARYL
CONJUGATED POLY-MERS
HALOGENATION
MONOMERS
PRODUCT OPTIMIZATION
title_short Improved synthesis of bis(chloromethyl)arene monomers
title_full Improved synthesis of bis(chloromethyl)arene monomers
title_fullStr Improved synthesis of bis(chloromethyl)arene monomers
title_full_unstemmed Improved synthesis of bis(chloromethyl)arene monomers
title_sort Improved synthesis of bis(chloromethyl)arene monomers
dc.creator.none.fl_str_mv Almassio, Marcela
Sarimbalis, Myrian N.
Garay, Raúl Oscar
author Almassio, Marcela
author_facet Almassio, Marcela
Sarimbalis, Myrian N.
Garay, Raúl Oscar
author_role author
author2 Sarimbalis, Myrian N.
Garay, Raúl Oscar
author2_role author
author
dc.subject.none.fl_str_mv BIS(HALOMETHYL)ARYL
CONJUGATED POLY-MERS
HALOGENATION
MONOMERS
PRODUCT OPTIMIZATION
topic BIS(HALOMETHYL)ARYL
CONJUGATED POLY-MERS
HALOGENATION
MONOMERS
PRODUCT OPTIMIZATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We report here on the experimental conditions for radical chlorination that provide improved yields of 2,5-bis(chloromethyl) pyridine and pyrazine, as well as on theoretical calculations which were performed in order to gain some insight regarding the factors that affect reactivity in these systems. The difficulties encountered previously in the methyl functionalization of N-heteroarenes are not due to radical selectivity that produces low yield of the dichlorides or to lower reactivity of this type of compounds, but to the post-halogenation reactions that occur on the desired products. Therefore, a careful handling during and after the reaction allowed us to find conditions for product optimization of α, α′-dichlorinated monomers.
Fil: Almassio, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Fil: Sarimbalis, Myrian N.. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Fil: Garay, Raúl Oscar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
description We report here on the experimental conditions for radical chlorination that provide improved yields of 2,5-bis(chloromethyl) pyridine and pyrazine, as well as on theoretical calculations which were performed in order to gain some insight regarding the factors that affect reactivity in these systems. The difficulties encountered previously in the methyl functionalization of N-heteroarenes are not due to radical selectivity that produces low yield of the dichlorides or to lower reactivity of this type of compounds, but to the post-halogenation reactions that occur on the desired products. Therefore, a careful handling during and after the reaction allowed us to find conditions for product optimization of α, α′-dichlorinated monomers.
publishDate 2005
dc.date.none.fl_str_mv 2005-12
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/11336/96981
Almassio, Marcela; Sarimbalis, Myrian N.; Garay, Raúl Oscar; Improved synthesis of bis(chloromethyl)arene monomers; Vsp Bv; Designed Monomers And Polymers; 8; 4; 12-2005; 287-296
1385-772X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/96981
identifier_str_mv Almassio, Marcela; Sarimbalis, Myrian N.; Garay, Raúl Oscar; Improved synthesis of bis(chloromethyl)arene monomers; Vsp Bv; Designed Monomers And Polymers; 8; 4; 12-2005; 287-296
1385-772X
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://www.tandfonline.com/doi/abs/10.1163/1568555054460024
info:eu-repo/semantics/altIdentifier/doi/10.1163/1568555054460024
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
dc.publisher.none.fl_str_mv Vsp Bv
publisher.none.fl_str_mv Vsp Bv
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_ 1844613139271778304
score 13.070432

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