Reaction of ortho-nitro-substituted benzene derivatives with ferrous oxalate

Abstract

The reaction of ferrous oxalate with methyl 4-(o-nitrophenyl)butyrate, methyl o-nitrophenoxyacetate, o-nitrocumene, o-t-butynitrobenzene, NN-dimethyl-o-nitroaniline, o-nitroanisole, and nitrocyclohexane at 215–260° gave a variety of compounds, including cyclisation products and primary amines. Most of the results may be interpreted in terms of the formation of nitrene intermediates, although other mechanisms such as the dehydration of aci-nitro-tautomers, where these are possible, may be operative.