SPECIFIC ORTHO ORIENTATION IN THE VICARIOUS SUBSTITUTION OF HYDROGEN IN AROMATIC NITRO COMPOUNDS WITH CARBANION OF CHLOROMETHYL PHENYL SULFONE

Article abstract of DOI:10.1016/S0040-4020(01)91141-X

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.