Rearrangement of imidoyl nitrates to N-nitro amides: an intramolecular [1,3] O-to-N migration of a nitro group
Abstract
Imidoyl nitrates, formed by the reaction of imidoyl chlorides with AgNO3, rearrange via a unimolecular, intramolecular mechanism probably involving homolytic fission of the O–N bond to yield N-nitro amides; migration of the nitro group in N-arylimidoyl nitrates to the ortho- and para-positions of the N-aryl ring does not involve a special ortho-directing effect.