3,3-Sigmatropic rearrangements involving N-O bond-cleavage of enehydroxylamine derivatives

Lucinda V. Reis, Ana M. Lobo, Sundaresan Prabhakar, Mariana P. Duarte

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)


Enehydroxylamines, derived from carbocyclic and heterocyclic 1,3-dioxo compounds, react with a variety of unsaturated electrophiles to give, in good to excellent yields, substances that in general undergo 3,3-sigmatropic rearrangements either spontaneously or upon heating. In those cases in which such reactions failed, addition of sodium hydride was found to induce the transformation. A study of the rearrangement by use of deuterium-labelled compounds showed that no crossover occurs, indicating the intramolecular nature of the process. The method provides 2,3- or 3,4-disubstituted cyclohexenones, 5,6-disubstituted barbiturates and the corresponding fused pyrrole and imidazolinone derivatives.

Original languageEnglish
Pages (from-to)190-208
Number of pages19
JournalEuropean Journal of Organic Chemistry
Issue number1
Publication statusPublished - 1 Jan 2003


  • Amines
  • Cleavage reactions
  • Sigmatropic rearrangement


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