TY - JOUR
T1 - 3,3-Sigmatropic rearrangements involving N-O bond-cleavage of enehydroxylamine derivatives
AU - Reis, Lucinda V.
AU - Lobo, Ana M.
AU - Prabhakar, Sundaresan
AU - Duarte, Mariana P.
PY - 2003/1/1
Y1 - 2003/1/1
N2 - 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.
AB - 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.
KW - Amines
KW - Cleavage reactions
KW - Sigmatropic rearrangement
UR - http://www.scopus.com/inward/record.url?scp=0037238464&partnerID=8YFLogxK
U2 - 10.1002/1099-0690(200301)2003:1<190::AID-EJOC190>3.0.CO;2-W
DO - 10.1002/1099-0690(200301)2003:1<190::AID-EJOC190>3.0.CO;2-W
M3 - Article
AN - SCOPUS:0037238464
SN - 1434-193X
SP - 190
EP - 208
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 1
ER -