Nitrosation of amides involves a pseudopericyclic 1,3-sigmatropic rearrangement

David M. Birney

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27 Scopus citations


Two possible pathways for the nitrosation of formamide and N-methyl formamide by nitrosonium ion (NO+) have been investigated at the B3LYP/6-31G(d,p) level. The key steps are pseudopericyclic 1,3-sigmatropic rearrangements to give the observed N-nitrosamides. The transition structures (8a and 8b) are close to planar on the amide moiety and have remarkably low barriers of only 6.6 and 4.8 kcal/mol from the lowest energy conformations of 6a and 6b, respectively.

Original languageEnglish
Pages (from-to)851-854
Number of pages4
JournalOrganic Letters
Issue number5
StatePublished - Mar 4 2004


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