The vicarious nucleophilic substitution of hydrogen proceeding via a cyclopropane ring-opening

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 sigma-adducts underwent base-induced elimination, resulting in cleavage of the cyclopropane ring. The ortho-substituted products can be directly transformed into substituted N-hydroxyindoles. (C) 1998 Elsevier Science Ltd. All rights reserved.