Exploiting Allenes: Synthesis and Reactivity of Strained Compounds

这个项目将继续探索联烯的化学性质，联烯是合成化学家的一个未被充分利用的官能团。 利用该部分的反应性导致发现了联烯炔的热[2 + 2]环加成反应，以提供亚烷基环丁烯，这是本提案的主题。在这项工作之前，这种不饱和的，紧张的部分的报告是罕见的。随时进入这个环系统将有助于研究它们的化学反应性和合成效用。 计算和合成研究将进行理解的热[2 + 2]环加成反应的联烯-炔的机制。该奖项将扩大联烯-炔的热[2 + 2]环加成反应的范围，并将探索亚烷基环丁烯的合成用途。有了这个奖项，有机和大分子化学计划将支持匹兹堡大学化学系Kay Brummond教授的研究。通过创新反应的发展发现和合成新的功能阵列是Brummond教授研究计划的主要目标。该提案目标的实现将提供对应变化合物化学的更全面的理解和化学空间的扩展，从而促进新的生物探针和药物的发现。

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.