UNEXPECTED REACTIVITY OF ALLYL MAGNESIUM CHLORIDE WITH NITROARENES. A GENERAL METHOD OF SYNTHESIS OF N-ALLYL-N-ARYLHYDROXYLAMINES AND N-ALLYLANILINES.

Article abstract of DOI:10.1016/S0040-4039(00)86724-6

In contrast to alkyl Grinard reagents, the allyl reagent reacts with nitroarenes via 1,2 addition to the nitro group.The "in situ" treatment of the unstable intermediate adduct with LiAlH4 in the presence of catalytic Pd/C provides a general synthesis of N-allyl-N-arylhydroxylamines or N-allylanilines.