Specific ortho orientation in the vicarious substitution of hydrogen in aromatic nitro compounds with carbanion of chloromethyl phenyl sulfone

M Makosza, T Glinka, A Kinowski

Index: Makosza, M.; Glinka, T.; Kinowski, A. Tetrahedron, 1984 , vol. 40, # 10 p. 1863 - 1868

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Citation Number: 47

Abstract

Vicarious nucleophilic substitution of hydrogen atoms in nitroarenes with chloromethylphenyl sulfone proceeds selectively ortho to the nitro group when carried out in t-BuOK/THF base/solvent system. In the majority of 3-substituted nitrobenzene derivatives substitution occurs at the most hindered position 2. These conditions offer an efficient method of synthesis of 2, 6 and 2, 3-disubstituted nitrobenzene derivatives.