A Meisenheimer complex is a sigma-bonded anionic addition species associated with suitable nucleophilic aromatic substitution reactions. Delocalization into ortho or para nitro groups can stabilize its negative charge.
A tethered nucleophile attacking the ipso carbon of an activated aromatic ring can form a cyclic sigma-adduct sharing one atom with that ring. Rearomatization then cleaves the original aryl–heteroatom bond.
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