Exploiting Allenes: Synthesis and Reactivity of Strained Compounds

利用丙二烯：应变化合物的合成和反应性

• 批准号: 0910597
• 负责人: Kay Brummond
• 金额: $ 42万
• 依托单位: University of Pittsburgh
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2009
• 资助国家: 美国
• 起止时间: 2009-08-01 至 2013-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0910597&HistoricalAwards=false
• 关键词: Exploiting; Allenes; Synthesis; Reactivity; Strained

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.

该项目将继续探索烯的化学性质，这是合成化学家的曲目中未充分利用的官能团。利用这部分的反应性，发现了一个烯炔的热[2 + 2]环加成反应，得到烷基烯环丁烯，这是本提案的主题。在这项工作之前，这种不饱和的，紧张的部分的报道是罕见的。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用途。将进行计算和合成研究，以了解烯炔热[2 + 2]环加成反应的机理。扩大了烯炔热[2 + 2]环加成反应的范围，探索了烷基烯环丁烯的合成用途。有了这个奖项，有机和大分子化学项目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。实现本提案的目标将提供对应变化合物的化学更一般的理解和化学空间的扩展，从而加强新的生物探针和药物的发现。