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Stable Spirocyclic Meisenheimer Complexes

Meisenheimer complexes are important intermediates in Nucleophilic Aromatic Substitution Reactions (S(N)Ar). They are formed by the addition of electron rich species to polynitro aromatic compounds or aromatic compounds with strong electron withdrawing groups. It is possible to distinguish two types...

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Autores principales: Al-Kaysi, Rabih O., Gallardo, Iluminada, Guirado, Gonzalo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245453/
https://www.ncbi.nlm.nih.gov/pubmed/18596655
http://dx.doi.org/10.3390/molecules13061282
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author Al-Kaysi, Rabih O.
Gallardo, Iluminada
Guirado, Gonzalo
author_facet Al-Kaysi, Rabih O.
Gallardo, Iluminada
Guirado, Gonzalo
author_sort Al-Kaysi, Rabih O.
collection PubMed
description Meisenheimer complexes are important intermediates in Nucleophilic Aromatic Substitution Reactions (S(N)Ar). They are formed by the addition of electron rich species to polynitro aromatic compounds or aromatic compounds with strong electron withdrawing groups. It is possible to distinguish two types of Meisenheimer or σ-complexes, the σ(H)-complex or σ(X)-complex (also named ipso), depending on the aromatic ring position attacked by the nucleophile (a non-substituted or substituted one, respectively). Special examples of σ(X)- or ipso-complexes are formed through intermediate spiro adducts, via intramolecular S(N)Ar. Some of these spirocyclic Meisenheimer complexes, a type of σ(X)-complex, are exceptionally stable in solution and/or as solids. They can be isolated and characterized using X-ray, and various spectroscopic techniques such as NMR, UV-Vis, IR, and fluorescence. A few of these stable spirocyclic Meisenheimer complexes are zwitterionic and exhibit interesting photophysical and redox properties. We will review recent advances, synthesis and potential applications of these stable spirocyclic Meisenheimer complexes.
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spelling pubmed-62454532018-11-26 Stable Spirocyclic Meisenheimer Complexes Al-Kaysi, Rabih O. Gallardo, Iluminada Guirado, Gonzalo Molecules Review Meisenheimer complexes are important intermediates in Nucleophilic Aromatic Substitution Reactions (S(N)Ar). They are formed by the addition of electron rich species to polynitro aromatic compounds or aromatic compounds with strong electron withdrawing groups. It is possible to distinguish two types of Meisenheimer or σ-complexes, the σ(H)-complex or σ(X)-complex (also named ipso), depending on the aromatic ring position attacked by the nucleophile (a non-substituted or substituted one, respectively). Special examples of σ(X)- or ipso-complexes are formed through intermediate spiro adducts, via intramolecular S(N)Ar. Some of these spirocyclic Meisenheimer complexes, a type of σ(X)-complex, are exceptionally stable in solution and/or as solids. They can be isolated and characterized using X-ray, and various spectroscopic techniques such as NMR, UV-Vis, IR, and fluorescence. A few of these stable spirocyclic Meisenheimer complexes are zwitterionic and exhibit interesting photophysical and redox properties. We will review recent advances, synthesis and potential applications of these stable spirocyclic Meisenheimer complexes. MDPI 2008-06-09 /pmc/articles/PMC6245453/ /pubmed/18596655 http://dx.doi.org/10.3390/molecules13061282 Text en © 2008 by the authors. Licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Review
Al-Kaysi, Rabih O.
Gallardo, Iluminada
Guirado, Gonzalo
Stable Spirocyclic Meisenheimer Complexes
title Stable Spirocyclic Meisenheimer Complexes
title_full Stable Spirocyclic Meisenheimer Complexes
title_fullStr Stable Spirocyclic Meisenheimer Complexes
title_full_unstemmed Stable Spirocyclic Meisenheimer Complexes
title_short Stable Spirocyclic Meisenheimer Complexes
title_sort stable spirocyclic meisenheimer complexes
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245453/
https://www.ncbi.nlm.nih.gov/pubmed/18596655
http://dx.doi.org/10.3390/molecules13061282
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