Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations

Autores
Kneeteman, Maria Nelida; Della Rosa, Claudia Daniela; Ormachea, Carla; Giménez, Paula; López Baena, Anna Francesca; Mancini, Pedro Maximo Emilio
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The cycloaddition reactions between nitronaphthalenes and 1-trimethylsilyloxy-1,3-butadiene produce phenantrenol derivatives as principal products. The primary adducts suffer the irreversible lost of nitrous acid and consequently, the aromatization. In these reactions it is frequent to observe the presence of naphtylpyrrole derivatives as a result of a hetero Diels-Alder process, which is competitive with the normal way. The global electrophilic character of the dienophile is responsible of these results. Other dienes with electron donor substitution in C-1 show a different behavior in which the hetero Diels-Alder products prevails. In the series explored only the substrate 1-ciano-4-nitronaphthalene produces the naphtylpyrrole derivative as principal product, probably as a consequence of its charge distribution. A combination between stereoelectronic effects in the electrophile and the type of substitution joint to the nucleophilicity of the diene is responsible of the results and regioselectivity observed in these polar cycloaddition reactions. In all the cases studied the regioselectivity expected by theoretical calculations corresponds with the ones obtained experimentally.
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: Della Rosa, Claudia Daniela. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina
Fil: Ormachea, Carla. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: Giménez, Paula. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: López Baena, Anna Francesca. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Materia
Phenanthrenols
Nitronaphthalenes
Diels-Alder Reaction
Electrophiles
Theoretical Calculations
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:11336/31445
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/31445
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical CalculationsKneeteman, Maria NelidaDella Rosa, Claudia DanielaOrmachea, CarlaGiménez, PaulaLópez Baena, Anna FrancescaMancini, Pedro Maximo EmilioPhenanthrenolsNitronaphthalenesDiels-Alder ReactionElectrophilesTheoretical Calculationshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The cycloaddition reactions between nitronaphthalenes and 1-trimethylsilyloxy-1,3-butadiene produce phenantrenol derivatives as principal products. The primary adducts suffer the irreversible lost of nitrous acid and consequently, the aromatization. In these reactions it is frequent to observe the presence of naphtylpyrrole derivatives as a result of a hetero Diels-Alder process, which is competitive with the normal way. The global electrophilic character of the dienophile is responsible of these results. Other dienes with electron donor substitution in C-1 show a different behavior in which the hetero Diels-Alder products prevails. In the series explored only the substrate 1-ciano-4-nitronaphthalene produces the naphtylpyrrole derivative as principal product, probably as a consequence of its charge distribution. A combination between stereoelectronic effects in the electrophile and the type of substitution joint to the nucleophilicity of the diene is responsible of the results and regioselectivity observed in these polar cycloaddition reactions. In all the cases studied the regioselectivity expected by theoretical calculations corresponds with the ones obtained experimentally.Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: Della Rosa, Claudia Daniela. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; ArgentinaFil: Ormachea, Carla. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: Giménez, Paula. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: López Baena, Anna Francesca. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaBentham Science Publishers2014-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31445Mancini, Pedro Maximo Emilio; López Baena, Anna Francesca; Giménez, Paula; Ormachea, Carla; Della Rosa, Claudia Daniela; Kneeteman, Maria Nelida; et al.; Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations; Bentham Science Publishers; Letters in Organic Chemistry; 11; 5; 2-2014; 333-3371570-1786CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.2174/1570178611666140123235852info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/119905/articleinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:41:24Zoai:ri.conicet.gov.ar:11336/31445instacron: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 09:41:25.249CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
title Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
spellingShingle Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
Kneeteman, Maria Nelida
Phenanthrenols
Nitronaphthalenes
Diels-Alder Reaction
Electrophiles
Theoretical Calculations
title_short Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
title_full Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
title_fullStr Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
title_full_unstemmed Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
title_sort Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations
dc.creator.none.fl_str_mv Kneeteman, Maria Nelida
Della Rosa, Claudia Daniela
Ormachea, Carla
Giménez, Paula
López Baena, Anna Francesca
Mancini, Pedro Maximo Emilio
author Kneeteman, Maria Nelida
author_facet Kneeteman, Maria Nelida
Della Rosa, Claudia Daniela
Ormachea, Carla
Giménez, Paula
López Baena, Anna Francesca
Mancini, Pedro Maximo Emilio
author_role author
author2 Della Rosa, Claudia Daniela
Ormachea, Carla
Giménez, Paula
López Baena, Anna Francesca
Mancini, Pedro Maximo Emilio
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Phenanthrenols
Nitronaphthalenes
Diels-Alder Reaction
Electrophiles
Theoretical Calculations
topic Phenanthrenols
Nitronaphthalenes
Diels-Alder Reaction
Electrophiles
Theoretical Calculations
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 cycloaddition reactions between nitronaphthalenes and 1-trimethylsilyloxy-1,3-butadiene produce phenantrenol derivatives as principal products. The primary adducts suffer the irreversible lost of nitrous acid and consequently, the aromatization. In these reactions it is frequent to observe the presence of naphtylpyrrole derivatives as a result of a hetero Diels-Alder process, which is competitive with the normal way. The global electrophilic character of the dienophile is responsible of these results. Other dienes with electron donor substitution in C-1 show a different behavior in which the hetero Diels-Alder products prevails. In the series explored only the substrate 1-ciano-4-nitronaphthalene produces the naphtylpyrrole derivative as principal product, probably as a consequence of its charge distribution. A combination between stereoelectronic effects in the electrophile and the type of substitution joint to the nucleophilicity of the diene is responsible of the results and regioselectivity observed in these polar cycloaddition reactions. In all the cases studied the regioselectivity expected by theoretical calculations corresponds with the ones obtained experimentally.
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: Della Rosa, Claudia Daniela. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina
Fil: Ormachea, Carla. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: Giménez, Paula. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: López Baena, Anna Francesca. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
description The cycloaddition reactions between nitronaphthalenes and 1-trimethylsilyloxy-1,3-butadiene produce phenantrenol derivatives as principal products. The primary adducts suffer the irreversible lost of nitrous acid and consequently, the aromatization. In these reactions it is frequent to observe the presence of naphtylpyrrole derivatives as a result of a hetero Diels-Alder process, which is competitive with the normal way. The global electrophilic character of the dienophile is responsible of these results. Other dienes with electron donor substitution in C-1 show a different behavior in which the hetero Diels-Alder products prevails. In the series explored only the substrate 1-ciano-4-nitronaphthalene produces the naphtylpyrrole derivative as principal product, probably as a consequence of its charge distribution. A combination between stereoelectronic effects in the electrophile and the type of substitution joint to the nucleophilicity of the diene is responsible of the results and regioselectivity observed in these polar cycloaddition reactions. In all the cases studied the regioselectivity expected by theoretical calculations corresponds with the ones obtained experimentally.
publishDate 2014
dc.date.none.fl_str_mv 2014-02
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/11336/31445
Mancini, Pedro Maximo Emilio; López Baena, Anna Francesca; Giménez, Paula; Ormachea, Carla; Della Rosa, Claudia Daniela; Kneeteman, Maria Nelida; et al.; Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations; Bentham Science Publishers; Letters in Organic Chemistry; 11; 5; 2-2014; 333-337
1570-1786
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31445
identifier_str_mv Mancini, Pedro Maximo Emilio; López Baena, Anna Francesca; Giménez, Paula; Ormachea, Carla; Della Rosa, Claudia Daniela; Kneeteman, Maria Nelida; et al.; Synthesis of Phenanthrenol Derivatives Through Polar Diels-Alder Reactions Employing Nitronaphthalenes and (E)-1-(Trimethylsilyloxy)-1,3- butadiene. Theoretical Calculations; Bentham Science Publishers; Letters in Organic Chemistry; 11; 5; 2-2014; 333-337
1570-1786
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.2174/1570178611666140123235852
info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/119905/article
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 Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
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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