title: Zn(II)- or Ag(I)-catalyzed 1,4-metathesis reactions between 3-En-1-ynamides and nitrosoarenes.
abstract: Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.
authors: Department of Chemistry, National Tsing-Hua University , Hsinchu, Taiwan, ROC.
authors: Sagar Ashok
authors: SA
authors: Gawade
authors: Deepak B
authors: DB
authors: Huple
authors: Rai-Shung
authors: RS
authors: Liu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D000480:Alkynes; D000577:Amides; D001547:Benzaldehydes; D009603:Nitroso Compounds; D012834:Silver; D015032:Zinc