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

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.