1246854-95-4Relevant articles and documents
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.