Gold-Catalyzed Rearrangement of Propargyl Alcohols Using Coupling Constants To Determine Isomeric Ratios

• Xinpeng Cheng ^[1] ; Jonna Chen ^[1] ; Morgan J. Gainer ^[1] ; Liming Zhang ^[1]
  1. [1] University of California, United States
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 10, 2019, págs. 2348-2351
• Idioma: inglés
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• Resumen

  • Gold is an increasingly prominent transition metal in organic synthesis. The air-stable, water-insensitive cationic gold(I) catalysts enable varieties of synthetic transformations with a simple reaction setup. However, this increased importance has not coincided with an increase in the application of gold in second-year organic chemistry courses. An experiment is described that includes a gold-catalyzed rearrangement of propargyl alcohols targeted at second-year organic chemistry students. The reaction produces a mixture of E and Z isomers of an enone product that students analyze by 1H NMR spectroscopy to determine the major product.