Exploiting Allenes: Synthesis and Reactivity of Strained Compounds

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This project will continue work to explore the chemistry of allenes, an underutilized functional group in the synthetic chemist's repertoire. Exploiting the reactivity of this moiety led to the discovery of a thermal [2 + 2] cycloaddition reaction of an allene-yne to afford an alkylidene cyclobutene, the topic of this proposal. Prior to this work, reports of this unsaturated, strained moiety were rare. Ready access to this ring system will facilitate investigations into their chemical reactivity and synthetic utility. Computational and synthetic studies will be undertaken to understand the mechanism of the thermal [2 + 2] cycloaddition reaction of allene-ynes. The scope of the thermal [2 + 2] cycloaddition reaction of allene-ynes will be expanded and the synthetic utility of alkylidene cyclobutenes will be explored.With this award the Organic and Macromolecular Chemistry Program is supporting the research of Professor Kay Brummond of the Department of Chemistry at the University of Pittsburgh. Discovery and synthesis of new arrays of functionality through the development of innovative reactions is the primary aim of Professor Brummond's research program. Realization of the goals of this proposal will provide a more general understanding of the chemistry of strained compounds and an expansion of chemical space, thus enhancing the discovery of new biological probes and pharmaceuticals.