Unexpected reactivity of allyl magnesium chloride with nitroarenes. A general method of synthesis of N-allyl-N-arylhydroxylamines and N-allylanilines

In contrast to alkyl Grignard reagents, the allyl reagent reacts with nitroarenes via 1,2-addition to the nitro grouop. 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