Copper-Mediated Vicarious Substitution of 1,3-Dinitrobenzene with lodophenols or lodomethyl Phenyl Sulfoxide/Sulfone

Olof Haglund; Abdul A. K. M. Hai; Martin Nilsson

doi:10.1055/s-1990-27061

Synthesis 1990; 1990(10): 942-944
DOI: 10.1055/s-1990-27061

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Copper-Mediated Vicarious Substitution of 1,3-Dinitrobenzene with lodophenols or lodomethyl Phenyl Sulfoxide/Sulfone

Olof Haglund^* , Abdul A. K. M. Hai, Martin Nilsson

^*Department of Organic Chemistry, Chalmers University of Technology, S-41296 Göteborg. Sweden

Abstract

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1,3-Dinitrobenzene reacts with 4-iodophenol or 2-iodophenol in the presence of copper(I) tert-butoxide and pyridine to give 2′,6′- dinitrobiphenyl-4-ol and 1-nitrodibenzofuran, respectively, in good yield. Similarly, iodomethyl phenyl sulfone or sulfoxide and 1,3-dinitrobenzene are selectively converted into 2,6-dinitrobenzyl phenyl sulfone and sulfoxide, respectively. We believe that the reactions proceed via Meisenheimer intermediates formed from 1,3-dinitrobenzene and the iodophenol, from which a proton and copper(I) iodide are eliminated. The result is a copper-mediated, selective vicarious nucleophilic substitution of hydrogen at C-2 of 1,3-dinitrobenzene.

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