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 of Meisenheimer or sigma-complexes, the sigma(H)-complex or sigma(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 sigma(X)- or ipso-complexes are formed through intermediate spiro adducts, via intramolecular SNAr. Some of these spirocyclic Meisenheimer complexes, a type of sigma(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.
Al-Kaysi
Rabih O
RO
Department of Basic Sciences, King Saud Bin Abdulaziz University for Health Sciences-National Guard Health Affairs, Riyadh 11423, Kingdom of Saudi Arabia. kaysir@ksau-hs.edu.sa
Gallardo
Iluminada
I
Guirado
Gonzalo
G
D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D010084:Oxidation-Reduction; D013057:Spectrum Analysis; D013141:Spiro Compounds / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D013141:Spiro Compounds