Reactions of organic anions. Part 109. Vicarious nucleophilic substitution of hydrogen in nitroarenes with carbanions of. alpha.-haloalkyl phenyl sulfones

M Makosza, J Golinski, J Baran

Index: Makosza, Mieczyslaw; Golinski, Jerzy; Baran, Janusz Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1488 - 1494

Full Text: HTML

Citation Number: 97

Abstract

Carbanions of a-chloroalkyl phenyl sulfones and NJV-diallryl-a-chloroalkanesulfonamides react with nitrobenzenes to effect direct nucleophilic replacement of hydrogen ortho and para to the nitro group, with vicarious loss of chloride anion, to give the corresponding nitrobenzylsulfonyl derivatives. The reaction occurs much more rapidly than the replacement of such good leaving groups as halogen, methoxy, and phenoxy. Most substituents in the ...