Electrophilic Aromatic Substitution - Ipso Substitution

Ipso Substitution

Ipso substitution a special case of electrophilic aromatic substitution where the leaving group is not hydrogen.

A classic example is the reaction of salicylic acid with a mixture of nitric and sulfuric acid to form picric acid. The nitration of the 2 position involves the loss of CO2 as the leaving group.

Desulfonation in which a sulfonyl group is substituted by a proton is a common example. See also Hayashi rearrangement.

In aromatics substituted by silicon, the silicon reacts by ipso substitution.

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