Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans

Autores
Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M. F.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Diels-Alder reactions between the substituted furans 1a-1c and Danishefsky's diene (2), yielding 5-hydroxybenzofurans, were studied by density functional theory [B3LYP/6-31G(d) level] in benzene as solvent (SP/CPCM). The mechanistic details of these reactions, especially with respect to regio-, site-, and stereochemistry were analyzed in detail. Moreover, the extrusion of nitrous acid from the Diels-Alder cycloadducts and the formation of the aromatic products were also explained in order to give a total description of the complete domino processes. Some Diels-Alder reactions leading to 5-hydroxybenzofurans were studied at the B3LYP/6-31G(d) level of theory in benzene as solvent (SP/CPCM). DFT calculations on the transition structures were carried out for all the possible reaction channels (site, regio-, and stereoisomeric channels were included in this study). Additionally, a description of the complete domino processes was performed.
Fil: Brasca, Romina. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina
Fil: Fabian, Walter M. F.. Karl Franzens Universität Graz,; Austria
Materia
Cycloaddition
Density Functional Calculations
Diels-Alder Reactions
Oxygen Heterocycles
Reaction Mechanisms
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:11336/73508
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofuransBrasca, RominaKneeteman, Maria NelidaMancini, Pedro Maximo EmilioFabian, Walter M. F.CycloadditionDensity Functional CalculationsDiels-Alder ReactionsOxygen HeterocyclesReaction Mechanismshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Diels-Alder reactions between the substituted furans 1a-1c and Danishefsky's diene (2), yielding 5-hydroxybenzofurans, were studied by density functional theory [B3LYP/6-31G(d) level] in benzene as solvent (SP/CPCM). The mechanistic details of these reactions, especially with respect to regio-, site-, and stereochemistry were analyzed in detail. Moreover, the extrusion of nitrous acid from the Diels-Alder cycloadducts and the formation of the aromatic products were also explained in order to give a total description of the complete domino processes. Some Diels-Alder reactions leading to 5-hydroxybenzofurans were studied at the B3LYP/6-31G(d) level of theory in benzene as solvent (SP/CPCM). DFT calculations on the transition structures were carried out for all the possible reaction channels (site, regio-, and stereoisomeric channels were included in this study). Additionally, a description of the complete domino processes was performed.Fil: Brasca, Romina. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; ArgentinaFil: Fabian, Walter M. F.. Karl Franzens Universität Graz,; AustriaWiley VCH Verlag2011-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/73508Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M. F.; Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans; Wiley VCH Verlag; European Journal of Organic Chemistry; 4; 2-2011; 721-7291434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201001196info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201001196info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:07:16Zoai:ri.conicet.gov.ar:11336/73508instacron: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 12:07:16.427CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
title Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
spellingShingle Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
Brasca, Romina
Cycloaddition
Density Functional Calculations
Diels-Alder Reactions
Oxygen Heterocycles
Reaction Mechanisms
title_short Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
title_full Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
title_fullStr Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
title_full_unstemmed Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
title_sort Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
dc.creator.none.fl_str_mv Brasca, Romina
Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M. F.
author Brasca, Romina
author_facet Brasca, Romina
Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M. F.
author_role author
author2 Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M. F.
author2_role author
author
author
dc.subject.none.fl_str_mv Cycloaddition
Density Functional Calculations
Diels-Alder Reactions
Oxygen Heterocycles
Reaction Mechanisms
topic Cycloaddition
Density Functional Calculations
Diels-Alder Reactions
Oxygen Heterocycles
Reaction Mechanisms
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Diels-Alder reactions between the substituted furans 1a-1c and Danishefsky's diene (2), yielding 5-hydroxybenzofurans, were studied by density functional theory [B3LYP/6-31G(d) level] in benzene as solvent (SP/CPCM). The mechanistic details of these reactions, especially with respect to regio-, site-, and stereochemistry were analyzed in detail. Moreover, the extrusion of nitrous acid from the Diels-Alder cycloadducts and the formation of the aromatic products were also explained in order to give a total description of the complete domino processes. Some Diels-Alder reactions leading to 5-hydroxybenzofurans were studied at the B3LYP/6-31G(d) level of theory in benzene as solvent (SP/CPCM). DFT calculations on the transition structures were carried out for all the possible reaction channels (site, regio-, and stereoisomeric channels were included in this study). Additionally, a description of the complete domino processes was performed.
Fil: Brasca, Romina. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina
Fil: Fabian, Walter M. F.. Karl Franzens Universität Graz,; Austria
description Diels-Alder reactions between the substituted furans 1a-1c and Danishefsky's diene (2), yielding 5-hydroxybenzofurans, were studied by density functional theory [B3LYP/6-31G(d) level] in benzene as solvent (SP/CPCM). The mechanistic details of these reactions, especially with respect to regio-, site-, and stereochemistry were analyzed in detail. Moreover, the extrusion of nitrous acid from the Diels-Alder cycloadducts and the formation of the aromatic products were also explained in order to give a total description of the complete domino processes. Some Diels-Alder reactions leading to 5-hydroxybenzofurans were studied at the B3LYP/6-31G(d) level of theory in benzene as solvent (SP/CPCM). DFT calculations on the transition structures were carried out for all the possible reaction channels (site, regio-, and stereoisomeric channels were included in this study). Additionally, a description of the complete domino processes was performed.
publishDate 2011
dc.date.none.fl_str_mv 2011-02
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/11336/73508
Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M. F.; Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans; Wiley VCH Verlag; European Journal of Organic Chemistry; 4; 2-2011; 721-729
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/73508
identifier_str_mv Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M. F.; Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans; Wiley VCH Verlag; European Journal of Organic Chemistry; 4; 2-2011; 721-729
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201001196
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201001196
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 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 12.982451

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