Olivia Gargiulo

Abstract:

The Hughes Research Group has previously described a novel tandem cycloaromatization of diynal compounds. This copper(I) catalyzed reaction in DMF solvent was shown to result in a number of different products, and the distribution of those products depends on the reaction conditions. A general mechanism has been proposed to explain the formation of the various products. When the solvent was changed to DMSO, a novel spirolactone product was identified and characterized. Using a Bronsted acid such as HOTs also resulted in similar product distribution to that observed with CuI, suggesting a similar mechanism. Another benzoquinone product was identified in many of the reaction conditions examined, and may represent a background oxidative pathway that operates regardless of solvent or catalyst.