Activated aromatic addition–elimination substitution
A nucleophile can add to an activated aryl system, forming an anionic intermediate before leaving-group elimination restores aromaticity.
Key knowledge
A nucleophile can add to an activated aryl system, forming an anionic intermediate before leaving-group elimination restores aromaticity. Electron-withdrawing groups in suitable positions can stabilize the intermediate in the representative nitroaryl-halide model. This is mechanistically different from both electrophilic aromatic substitution and ordinary saturated-carbon SN2 displacement.
Conditions and scope
- The record covers the activated addition–elimination model; benzyne, concerted and catalytic substitutions are distinct routes.
- Aryl substitution is not limited universally to one activating group or one leaving group.
Sources · 1
References
Sources retain their recorded scope. A source link alone does not establish verification of every statement.
Evidence and review
Read resonance-stabilized anion and ortho/para nitro examples; excluded textbook's only-if wording as a universal limit on all aromatic substitution.
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Entry details
Permanent link to this entry ↗- Record identity
- uni-chem-nucleophilic-aromatic-substitution
- Revision
- core.1
- Structured reference record
- University core expansion