N-[2-(hydroxymethyl)phenyl]pyrrole was found to be amenable to selective a-metalation. Trapping with a variety of electrophilic reagents afforded the expected products with moderate to high yields. Derivs. formed by treatment of the organometallic intermediate with aldehydes, ketones or carbon dioxide could be cyclized to give pyrrolobenzoxazepines. e.g., I (R = Ph, R1 = H, Me, Ph; R = CO2Me, R1 = Me; R = R1 = Me). [on SciFinder (R)]