The Chemistry of Aryllead(IV) Tricarboxylates. The C-Arylation of Nitroalkanes and Nitronate Salts with Aryllead Triacetates

Abstract

2-Nitropropane reacts with phenyllead triacetate in dimethyl sulfoxide to give 2-nitro-2-phenylpropane in good yield. This arylation of nitroalkanes has been examined with a variety of substrates and a number of aryllead triacetates, and in those cases where there was no steric hindrance the reaction was found to be quit general. Reactions of nitroethane and methyl nitroacetate, compounds with two α- hydrogens, were readily controlled to give either the mono- or di-arylated products. The corresponding nitronate salts were also examined and found to undergo the arylation reaction in similar yield but at a very much faster rate.