Rearrangement of Imidoyl Nitrates to N-Nitro Amides: an Intramolecular O-to-N Migration of a Nitro Group

DOI: 10.1039/c39880001249

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1249 - 1250 (1988)

Update date:2022-07-29

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Authors:

Carvalho, Emilia

Iley, Jim

Rosa, Eduarda

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Article abstract of DOI:10.1039/c39880001249

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.

Full text of DOI:10.1039/c39880001249

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