Module 6 : Aromatic Nucleophilic Substitution

Lecture 15 : Aromatic Nucleophilic Substitution

6.5.2 Bucherer Reaction

Some phenols proceed reaction with aqueous ammonium nitrite to give aromatic amines. The reactions are believed to take place via sulfite adduct of the keto-tautomer of phenol. Similarly, certain aromatic amines can be converted into phenols.

Proposed Mechanism

Examples: