Rearrangement of imidoyl nitrates to N-nitro amides: an intramolecular [1, 3] O-to-N migration of a nitro group

E Carvalho, J Iley, E Rosa

Index: Carvalho, Emilia; Iley, Jim; Rosa, Eduarda Journal of the Chemical Society, Chemical Communications, 1988 , # 18 p. 1249 - 1250

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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.