Triarylmethanes and their Medium‐Ring Analogues by Unactivated Truce–Smiles Rearrangement of Benzanilides

Intramolecular nucleophilic aromatic substitution (Truce–Smiles rearrangement) of the anions 2-benzyl benzanilides leads to triarylmethanes in an operationally simple manner. The reaction succeeds even without electronic activation ring that plays role electrophile SNAr reaction, being accelerated instead by preferred conformation imposed tertiary amide tether. substituent product may be removed or transformed into alternative functional groups. A ring-expanding variant (n n+4) provided a route doubly benzo-fused medium lactams 10 11 members. Hammett analysis returned ρ value consistent with operation partially concerted mechanism.