Mira Deshpande

Abstract:

This past summer, the work done focused on the reaction of a symmetrical compound containing two alkyne and two aldehyde functional groups. In this reaction the carbons in the alkyne functional groups became incorporated into new aromatic rings, but a variety of different products is usually observed. The ratios for these different polyaromatic hydrocarbon products can be influenced by the solvent, catalysts and temperature on the cyclization mechanism. The use of other metal catalysts did not yield clean or reproducible results. A kinetic analysis for the formation of one product, the naphthoquinone, revealed it to be autocatalytic. Analogs of the compound containing different substituents were synthesized and will be studied in comparison to the parent compound. Future work will continue to probe the autocatalytic mechanism of formation for the naphthoquinone, altering reaction conditions with the goal of more selective yields, and shift focus to a system containing two ketone functional groups in place of the two aldehydes.