1246854-90-9Relevant academic research and scientific papers
Synthesis of O-2-(acyl)vinylketoximes and their unusual rearrangements into 2- and 3-acyl-substituted pyrroles
Glotova, Tatyana E.,Schmidt, Elena Yu.,Dvorko, Marina Yu.,Ushakov, Igor A.,Mikhaleva, Al'Bina I.,Trofimov, Boris A.
supporting information; experimental part, p. 6189 - 6191 (2011/01/04)
-2-(Acyl)vinylketoximes (freshly prepared from ketoximes and acylacetylenes in the presence of Ph3P as catalyst in up to 83% yields) rearrange upon heating (125-150 °C) to give 2- or 3-acylpyrroles, wherein the positions of the acyl substituent
Triphenylphosphine as an effective catalyst for ketoximes addition to acylacetylenes: Regio- and stereospecific synthesis of (E)-(O)-2-(acyl) vinylketoximes
Trofimov, Boris A.,Glotova, Tatyana E.,Dvorko, Marina Yu.,Ushakov, Igor A.,Schmidt, Elena Yu.,Mikhaleva, Al'Bina I.
experimental part, p. 7527 - 7532 (2010/12/20)
Triphenylphosphine catalyzes the regio- and stereospecific addition of ketoximes to acylacetylenes, whereas classical conditions using acetylene (KOH/DMSO, 70 °C) are unsuitable for this purpose. The reaction proceeds under mild conditions (CH2Cl2, rt, 7 h) to afford (E)-(O)-2-(acyl)vinylketoximes (92-98% stereoselectivity) in a yield of up to 85%. The (E)-adducts obtained are energetically less favorable than the corresponding (Z)-isomers and are gradually enriched with (Z)-isomers, thus indicating the kinetic control of (E)-stereoselectivity of the reaction.
