156300-91-3Relevant academic research and scientific papers
3,3-Sigmatropic rearrangements involving N-O bond-cleavage of enehydroxylamine derivatives
Reis, Lucinda V.,Lobo, Ana M.,Prabhakar, Sundaresan,Duarte, Mariana P.
, p. 190 - 208 (2007/10/03)
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. Wiley-VCH Verlag GmbH & Co KGAA, 69451 Weinheim, Germany, 2003.
