The reaction of ortho-dinitrobenzenes with sodium borohydride

Abstract

The reaction of o-dinitrobenzene with sodium borohydride in aqueous dimethyl sulphoxide at room temperature gives nitrobenzene and benzofurazan in low yields. Deuterium is incorporated specifically into the ortho position of nitrobenzene when the reaction is performed with sodium borodeuteride. 2,3-Dinitrotoluene gives mainly m-nitrotoluene, but 3,4-dinitrotoluene gives both m- and p-nitrotoluenes.