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.
|Number of pages||19|
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - 1 Jan 2003|
- Cleavage reactions
- Sigmatropic rearrangement