Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid

Autores
Scoccia, Jimena; Gerbino, Darío César; Terraza, Victor Fabricio; Zuñiga, Adriana Elena; Podestá, Julio Cesar
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The preparation of symmetrical unsaturated diesters of dioe first was the reaction of mixed anhydrides, obtained from α,β-unsaturated acids and benzoyl chloride, with diols 3 (primary), 5 (secondary), and 7 (primary), i.e., Yamaguchi-SantaLucía's method, however only the symmetrical diacrylates of diols 5 and 7 were obtained quantitatively. In the other ten cases studied the reactions led to mixtures of symmetrical and unsymmetrical diesters that were difficult to separate. The mixed anhydrides did not react with the tertiary diols 4 (TADDOL) and 8. The average yield obtained in desired symmetrical diesters in the 12 cases studied was 54 %. The acylation of the diols with the anhydrides of the unsaturated acids, was found to be an excellent method, leading to the symmetrical unsaturated diesters of diols 3, 5, 7 as the only products of reaction, in an average yield of 83 %. Unfortunately, the method could not be applied to diesters derived from the tertiary diols 4 (TADDOL) and 8. The third method studied was the reaction between the alkoxides prepared with solutions of nBuLi in ether with the unsaturated acid chlorides at-50 °C, i.e., the Kaiser-Woodruff protocol. This was found to be the best of the three methods tested. The method was applied with success to the synthesis of the desired unsaturated diesters derived from diols 3-5, 7, and 8. The average yield of the 19 cases studied was 78 %.
Fil: Scoccia, Jimena. 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
Fil: Gerbino, Darío César. 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
Fil: Terraza, Victor Fabricio. 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
Fil: Zuñiga, Adriana Elena. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. 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
Materia
DIOLS
SYMMETRICAL UNSATURATED DIESTERS
SYNTHETIC METHODS
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:11336/85800
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/85800
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acidScoccia, JimenaGerbino, Darío CésarTerraza, Victor FabricioZuñiga, Adriana ElenaPodestá, Julio CesarDIOLSSYMMETRICAL UNSATURATED DIESTERSSYNTHETIC METHODShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The preparation of symmetrical unsaturated diesters of dioe first was the reaction of mixed anhydrides, obtained from α,β-unsaturated acids and benzoyl chloride, with diols 3 (primary), 5 (secondary), and 7 (primary), i.e., Yamaguchi-SantaLucía's method, however only the symmetrical diacrylates of diols 5 and 7 were obtained quantitatively. In the other ten cases studied the reactions led to mixtures of symmetrical and unsymmetrical diesters that were difficult to separate. The mixed anhydrides did not react with the tertiary diols 4 (TADDOL) and 8. The average yield obtained in desired symmetrical diesters in the 12 cases studied was 54 %. The acylation of the diols with the anhydrides of the unsaturated acids, was found to be an excellent method, leading to the symmetrical unsaturated diesters of diols 3, 5, 7 as the only products of reaction, in an average yield of 83 %. Unfortunately, the method could not be applied to diesters derived from the tertiary diols 4 (TADDOL) and 8. The third method studied was the reaction between the alkoxides prepared with solutions of nBuLi in ether with the unsaturated acid chlorides at-50 °C, i.e., the Kaiser-Woodruff protocol. This was found to be the best of the three methods tested. The method was applied with success to the synthesis of the desired unsaturated diesters derived from diols 3-5, 7, and 8. The average yield of the 19 cases studied was 78 %.Fil: Scoccia, Jimena. 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; ArgentinaFil: Gerbino, Darío César. 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; ArgentinaFil: Terraza, Victor Fabricio. 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; ArgentinaFil: Zuñiga, Adriana Elena. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Podestá, Julio Cesar. 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; ArgentinaWiley VCH Verlag2013-07info: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/11336/85800Scoccia, Jimena; Gerbino, Darío César; Terraza, Victor Fabricio; Zuñiga, Adriana Elena; Podestá, Julio Cesar; Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid; Wiley VCH Verlag; European Journal of Organic Chemistry; 20; 7-2013; 4418-44261434-193X1099-0690CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201300130info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201300130info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:02:57Zoai:ri.conicet.gov.ar:11336/85800instacron: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 10:02:57.78CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
title Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
spellingShingle Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
Scoccia, Jimena
DIOLS
SYMMETRICAL UNSATURATED DIESTERS
SYNTHETIC METHODS
title_short Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
title_full Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
title_fullStr Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
title_full_unstemmed Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
title_sort Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid
dc.creator.none.fl_str_mv Scoccia, Jimena
Gerbino, Darío César
Terraza, Victor Fabricio
Zuñiga, Adriana Elena
Podestá, Julio Cesar
author Scoccia, Jimena
author_facet Scoccia, Jimena
Gerbino, Darío César
Terraza, Victor Fabricio
Zuñiga, Adriana Elena
Podestá, Julio Cesar
author_role author
author2 Gerbino, Darío César
Terraza, Victor Fabricio
Zuñiga, Adriana Elena
Podestá, Julio Cesar
author2_role author
author
author
author
dc.subject.none.fl_str_mv DIOLS
SYMMETRICAL UNSATURATED DIESTERS
SYNTHETIC METHODS
topic DIOLS
SYMMETRICAL UNSATURATED DIESTERS
SYNTHETIC METHODS
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 preparation of symmetrical unsaturated diesters of dioe first was the reaction of mixed anhydrides, obtained from α,β-unsaturated acids and benzoyl chloride, with diols 3 (primary), 5 (secondary), and 7 (primary), i.e., Yamaguchi-SantaLucía's method, however only the symmetrical diacrylates of diols 5 and 7 were obtained quantitatively. In the other ten cases studied the reactions led to mixtures of symmetrical and unsymmetrical diesters that were difficult to separate. The mixed anhydrides did not react with the tertiary diols 4 (TADDOL) and 8. The average yield obtained in desired symmetrical diesters in the 12 cases studied was 54 %. The acylation of the diols with the anhydrides of the unsaturated acids, was found to be an excellent method, leading to the symmetrical unsaturated diesters of diols 3, 5, 7 as the only products of reaction, in an average yield of 83 %. Unfortunately, the method could not be applied to diesters derived from the tertiary diols 4 (TADDOL) and 8. The third method studied was the reaction between the alkoxides prepared with solutions of nBuLi in ether with the unsaturated acid chlorides at-50 °C, i.e., the Kaiser-Woodruff protocol. This was found to be the best of the three methods tested. The method was applied with success to the synthesis of the desired unsaturated diesters derived from diols 3-5, 7, and 8. The average yield of the 19 cases studied was 78 %.
Fil: Scoccia, Jimena. 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
Fil: Gerbino, Darío César. 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
Fil: Terraza, Victor Fabricio. 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
Fil: Zuñiga, Adriana Elena. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. 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
description The preparation of symmetrical unsaturated diesters of dioe first was the reaction of mixed anhydrides, obtained from α,β-unsaturated acids and benzoyl chloride, with diols 3 (primary), 5 (secondary), and 7 (primary), i.e., Yamaguchi-SantaLucía's method, however only the symmetrical diacrylates of diols 5 and 7 were obtained quantitatively. In the other ten cases studied the reactions led to mixtures of symmetrical and unsymmetrical diesters that were difficult to separate. The mixed anhydrides did not react with the tertiary diols 4 (TADDOL) and 8. The average yield obtained in desired symmetrical diesters in the 12 cases studied was 54 %. The acylation of the diols with the anhydrides of the unsaturated acids, was found to be an excellent method, leading to the symmetrical unsaturated diesters of diols 3, 5, 7 as the only products of reaction, in an average yield of 83 %. Unfortunately, the method could not be applied to diesters derived from the tertiary diols 4 (TADDOL) and 8. The third method studied was the reaction between the alkoxides prepared with solutions of nBuLi in ether with the unsaturated acid chlorides at-50 °C, i.e., the Kaiser-Woodruff protocol. This was found to be the best of the three methods tested. The method was applied with success to the synthesis of the desired unsaturated diesters derived from diols 3-5, 7, and 8. The average yield of the 19 cases studied was 78 %.
publishDate 2013
dc.date.none.fl_str_mv 2013-07
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/11336/85800
Scoccia, Jimena; Gerbino, Darío César; Terraza, Victor Fabricio; Zuñiga, Adriana Elena; Podestá, Julio Cesar; Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid; Wiley VCH Verlag; European Journal of Organic Chemistry; 20; 7-2013; 4418-4426
1434-193X
1099-0690
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85800
identifier_str_mv Scoccia, Jimena; Gerbino, Darío César; Terraza, Victor Fabricio; Zuñiga, Adriana Elena; Podestá, Julio Cesar; Synthesis of unsaturated diesters of primary, secondary and tertiary diols derived from dimethyl (+)-tartrate and galactaric acid; Wiley VCH Verlag; European Journal of Organic Chemistry; 20; 7-2013; 4418-4426
1434-193X
1099-0690
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://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201300130
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201300130
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.070432

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