The Vicarious Nucleophilic Substitution of Hydrogen Proceeding via a Cyclopropane Ring-Opening.

Abstract 1-Cyano-2,2-diethoxycarbonyl cyclopropane was reacted with several nitroarenes under basic conditions. The reaction proceeded according to the vicarious nucleophilic substitution of hydrogen scheme; i.e. the initially formed σ-adducts underwent base-induced elimination, resulting in cleavage of the cyclopropane ring. The ortho -substituted products can be directly transformed into substituted N -hydroxyindoles.