Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study

The Diels-Alder reaction is considered a pericyclic procces. However, depending of the structure of the diene and the dienophile the nature of this reaction can change. In the last years we have worked with aromatic nitro substituted compounds as electrophile in cycloaddition reactions with differen...

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Autores: Ormachea, Carla, Kneeteman, Maria Nelida, Mancini, Pedro
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2014
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/15753
Acceso en línea:http://hdl.handle.net/11336/15753
Access Level:acceso abierto
Palabra clave:Diels-Alder
Dft
Solvent Effects
Microwave Irradiation
Polar
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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spelling Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical StudyOrmachea, CarlaKneeteman, Maria NelidaMancini, PedroDiels-AlderDftSolvent EffectsMicrowave IrradiationPolarhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The Diels-Alder reaction is considered a pericyclic procces. However, depending of the structure of the diene and the dienophile the nature of this reaction can change. In the last years we have worked with aromatic nitro substituted compounds as electrophile in cycloaddition reactions with different dienes of diverse nucleophilicity. In that direction, it was used carbocyclic -nitronaphthalenes- and heterocyclic -nitropyrroles, nitrofuranes, nitrothiophenes, nitroselenophenes, nitroindoles, nitrobenzofuranes, and nitrobenzothiophnes-, in both cases mono and disubstituted. The dienes used were Danishefkys´diene, Rawals?diene, 1-trimethylsyliloxy-1,3-butadiene, and isoprene. Those monosubstituted electrophiles which aromatic character is higher -e.g. nitronaphthalene and nitrothiophenes- follow an heterocyclic cycloaddition channel and offer in its rections with the less nucleophilic dienes a pyrrolyl derivative as principal product, instead the others electrophiles follow a normal cycloaddition channel. In all these reactions the solvent effect was important. In thermal conditions we observed a great influence of ionic liquids (ILs) respect to the molecular solvents.This fact persuade us to consider these processes as polar Diels-Alder reactions in which and in a simple interpretation react an electrophile with a nucleophile. On the other hand when it was used microwave irradiation the best resold was obtained in free solvent conditions. We confirm this approach using theoretical calculations based on Density Functional Theory (DFT).Fil: Ormachea, Carla. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaFil: Mancini, Pedro. Universidad Nacional del Litoral. Facultad de Ingeniería Química. Departamento de Química Orgánica; ArgentinaThe Research Trends Editorial2014-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/15753Ormachea, Carla; Kneeteman, Maria Nelida; Mancini, Pedro; Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study; The Research Trends Editorial; Trends in Organic Chemistry; 17; 11-2014; 73-910972-4362enginfo:eu-repo/semantics/altIdentifier/url/http://www.researchtrends.net/tia/abstract.asp?in=0&vn=17&tid=14&aid=5717&pub=2014&type=info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:09:41Zoai:ri.conicet.gov.ar:11336/15753instacron: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:34982024-05-08 14:09:41.888CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
title Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
spellingShingle Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
Ormachea, Carla
Diels-Alder
Dft
Solvent Effects
Microwave Irradiation
Polar
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
title_full Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
title_fullStr Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
title_full_unstemmed Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
title_sort Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study
dc.creator.none.fl_str_mv Ormachea, Carla
Kneeteman, Maria Nelida
Mancini, Pedro
author Ormachea, Carla
author_facet Ormachea, Carla
Kneeteman, Maria Nelida
Mancini, Pedro
author_role author
author2 Kneeteman, Maria Nelida
Mancini, Pedro
author2_role author
author
dc.subject.none.fl_str_mv Diels-Alder
Dft
Solvent Effects
Microwave Irradiation
Polar
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Diels-Alder
Dft
Solvent Effects
Microwave Irradiation
Polar
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description The Diels-Alder reaction is considered a pericyclic procces. However, depending of the structure of the diene and the dienophile the nature of this reaction can change. In the last years we have worked with aromatic nitro substituted compounds as electrophile in cycloaddition reactions with different dienes of diverse nucleophilicity. In that direction, it was used carbocyclic -nitronaphthalenes- and heterocyclic -nitropyrroles, nitrofuranes, nitrothiophenes, nitroselenophenes, nitroindoles, nitrobenzofuranes, and nitrobenzothiophnes-, in both cases mono and disubstituted. The dienes used were Danishefkys´diene, Rawals?diene, 1-trimethylsyliloxy-1,3-butadiene, and isoprene. Those monosubstituted electrophiles which aromatic character is higher -e.g. nitronaphthalene and nitrothiophenes- follow an heterocyclic cycloaddition channel and offer in its rections with the less nucleophilic dienes a pyrrolyl derivative as principal product, instead the others electrophiles follow a normal cycloaddition channel. In all these reactions the solvent effect was important. In thermal conditions we observed a great influence of ionic liquids (ILs) respect to the molecular solvents.This fact persuade us to consider these processes as polar Diels-Alder reactions in which and in a simple interpretation react an electrophile with a nucleophile. On the other hand when it was used microwave irradiation the best resold was obtained in free solvent conditions. We confirm this approach using theoretical calculations based on Density Functional Theory (DFT).
publishDate 2014
dc.date.none.fl_str_mv 2014-11
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/11336/15753
Ormachea, Carla; Kneeteman, Maria Nelida; Mancini, Pedro; Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study; The Research Trends Editorial; Trends in Organic Chemistry; 17; 11-2014; 73-91
0972-4362
url http://hdl.handle.net/11336/15753
identifier_str_mv Ormachea, Carla; Kneeteman, Maria Nelida; Mancini, Pedro; Pseudo-Pericyclic Reactions: Aromatic Compound Derivatives as Electrophiles in Polar Diels-Alder Reactions. An Experimental and Theoretical Study; The Research Trends Editorial; Trends in Organic Chemistry; 17; 11-2014; 73-91
0972-4362
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.researchtrends.net/tia/abstract.asp?in=0&vn=17&tid=14&aid=5717&pub=2014&type=
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 The Research Trends Editorial
publisher.none.fl_str_mv The Research Trends Editorial
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15.811543

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