Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines

The reaction of the regioisomeric nitroanilines with KI and HNOs/bentonite system using microwave energy in solvent-free conditions is reported. In accordance with the obtained results, an unusual competence between nucleophilic aromatic substitution versus electrophilic aromatic substitution was de...

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Autores: Alvarez-Toledano, C, Aguilar-Pacheco, R, Baldovino-Pantaleon, O, Gutierrez-Perez, R, Miranda-Ruvalcaba, R, Penieres-Carrillo, G
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2000
País:México
Institución:Universidad Nacional Autónoma de México
Repositorio:Sistema de Información de la Facultad de Ciencias, UNAM
OAI Identifier:oai:repositorio.fciencias.unam.mx:11154/2012
Acceso en línea:http://hdl.handle.net/11154/2012
Access Level:acceso abierto
Palabra clave:Chemistry, Physical
nitroanilines
bentonite
nucleophilic
electrophilic
substitution
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spelling Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilinesAlvarez-Toledano, CAguilar-Pacheco, RBaldovino-Pantaleon, OGutierrez-Perez, RMiranda-Ruvalcaba, RPenieres-Carrillo, GChemistry, PhysicalnitroanilinesbentonitenucleophilicelectrophilicsubstitutionThe reaction of the regioisomeric nitroanilines with KI and HNOs/bentonite system using microwave energy in solvent-free conditions is reported. In accordance with the obtained results, an unusual competence between nucleophilic aromatic substitution versus electrophilic aromatic substitution was detected. With the para isomer two products were obtained, one for each reaction typehowever, with the meta-nitroaniline, only the nucleophilic substitution product was detected, and finally with the ortho isomer in addition to the nucleophilic and electrophilic substitution products, we detected the formation of 2,4-diiodonitrobenzene. In order to explain the achieved products, we propose that the last product is formed in two steps: firstly by a nucleophilic aromatic substitution, and secondly by an electrophilic aromatic substitution. (C) 2000 Elsevier Science B.V. All rights reserved.2011-01-22T10:27:28Z2011-01-22T10:27:28Z2000info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article1381-1169http://hdl.handle.net/11154/20122413164(40575):85-89reponame:Sistema de Información de la Facultad de Ciencias, UNAMinstname:Universidad Nacional Autónoma de Méxicoinstacron:UNAMenJournal of Molecular Catalysis A-Chemicalinfo:eu-repo/semantics/openAccessoai:repositorio.fciencias.unam.mx:11154/20122025-09-17T19:20:41Z
dc.title.none.fl_str_mv Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
title Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
spellingShingle Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
Alvarez-Toledano, C
Chemistry, Physical
nitroanilines
bentonite
nucleophilic
electrophilic
substitution
title_short Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
title_full Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
title_fullStr Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
title_full_unstemmed Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
title_sort Unusual nucleophilic versus electrophilic aromatic substitution on nitroanilines
dc.creator.none.fl_str_mv Alvarez-Toledano, C
Aguilar-Pacheco, R
Baldovino-Pantaleon, O
Gutierrez-Perez, R
Miranda-Ruvalcaba, R
Penieres-Carrillo, G
author Alvarez-Toledano, C
author_facet Alvarez-Toledano, C
Aguilar-Pacheco, R
Baldovino-Pantaleon, O
Gutierrez-Perez, R
Miranda-Ruvalcaba, R
Penieres-Carrillo, G
author_role author
author2 Aguilar-Pacheco, R
Baldovino-Pantaleon, O
Gutierrez-Perez, R
Miranda-Ruvalcaba, R
Penieres-Carrillo, G
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Chemistry, Physical
nitroanilines
bentonite
nucleophilic
electrophilic
substitution
topic Chemistry, Physical
nitroanilines
bentonite
nucleophilic
electrophilic
substitution
description The reaction of the regioisomeric nitroanilines with KI and HNOs/bentonite system using microwave energy in solvent-free conditions is reported. In accordance with the obtained results, an unusual competence between nucleophilic aromatic substitution versus electrophilic aromatic substitution was detected. With the para isomer two products were obtained, one for each reaction type
publishDate 2000
dc.date.none.fl_str_mv 2000
2011-01-22T10:27:28Z
2011-01-22T10:27:28Z
dc.type.none.fl_str_mv info:eu-repo/semantics/publishedVersion
info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv 1381-1169
http://hdl.handle.net/11154/2012
2413
identifier_str_mv 1381-1169
2413
url http://hdl.handle.net/11154/2012
dc.language.none.fl_str_mv en
language_invalid_str_mv en
dc.relation.none.fl_str_mv Journal of Molecular Catalysis A-Chemical
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv 164(40575):85-89
reponame:Sistema de Información de la Facultad de Ciencias, UNAM
instname:Universidad Nacional Autónoma de México
instacron:UNAM
instname_str Universidad Nacional Autónoma de México
instacron_str UNAM
institution UNAM
reponame_str Sistema de Información de la Facultad de Ciencias, UNAM
collection Sistema de Información de la Facultad de Ciencias, UNAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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