 Dearomatizing spirocyclization of a phenoxide

A para-tethered phenoxide can react through its carbon-nucleophilic resonance contributor. Intramolecular displacement of a tether leaving group at the para carbon creates a spiro ring and a cyclohexadienone. Subsequent acid-induced bond migration to a neighbouring carbon can expand the attached ring and restore the phenol. The two-stage sequence can therefore give a final substitution position different from the initial carbon attack.