RUI: Effects of Cationic Substituents on the Cope Rearrangement

在化学系有机动力学计划的支持下，泽维尔大学化学系的凯瑟琳·摩根开始研究COPE重排，这是一种通过1，5-己二烯的重组以高区域和立体选择性生成新的碳-碳键的反应。本研究的目的是确定在反应体系的反应核心上加入阳离子取代基是否可以加快反应速度。碳-碳键的形成是有机化学的核心，但构建碳-碳键的方法有限。碳基骨架的形成往往是合成过程中的一大挑战。Cope重排在合成中已经得到了大量的研究和开发，但我们仍然不能断言它已经被完全理解或在合成应用中发挥了它的全部潜力。1，5-己二烯在3位含吸电子基团的COPE重排反应的实验和理论研究是一个明确的项目，有可能对这一重排反应产生基本的见解，并扩大该反应的全部合成用途。由于碳-碳键的重要性，本项目创造性地将文献、理论和湿化学相结合，以增加对化学的理解并产生新的方法。泽维尔大学化学系的凯瑟琳·摩根教授将在有机动力学项目的支持下，在一所历史上黑人的本科生大学(HBCU)进行她的研究。本科生有能力完成大部分拟议的研究。初步结果是由摩根教授之前所在机构的十几名本科生获得的。代表不足的学生将有机会参与这项基础研究的所有方面，包括使用一系列已知程序合成有机化合物、开发新反应、提纯和表征产品、通过光谱分析确定反应速率以及计算研究。

With the support of the Organic Dynamics Program in the Chemistry Division, Kathleen Morgan of the Department of Chemistry at Xavier has begun a study of the Cope Rearrangement, which is a reaction where new carbon-carbon bonds are made with high regio- and stereo selectivity, via the reorganization of a 1,5-hexadiene. The goal of this study is to determine whether the reaction rate can be accelerated with the attachment of cationic substituents on the reactive core of the system. The formation of carbon-carbon bonds is at the heart of organic chemistry, yet there are a limited number of ways to construct them. The creation of the carbon-based skeleton often represents much of the challenge in synthesis. The Cope Rearrangement has been much studied and heavily exploited in synthesis and yet we are still not able to claim that it is fully understood or that it has reached its full potential in synthetic applications. The experimental and theoretical study of the Cope rearrangement of 1,5 hexadienes bearing electron-withdrawing groups at the 3 position is a well-defined project that has the potential to yield fundamental insights into this rearrangement and extend the full synthetic utility of this reaction. Because of the importance of carbon-carbon bond making, this project creatively blends literature, theory, and wet chemistry in order to increase understanding of the chemistry and produce novel methodology. .Professor Kathleen Morgan, of the Department of Chemistry at Xavier University, with the support of the Organic Dynamics Program, will conducted her research at an historically black undergraduate university (HBCU). Undergraduates are capable of performing the majority of the proposed research. The preliminary results were obtained by more than a dozen undergraduates at Professor Morgan's previous institution. Underrepresented students will have the opportunity to participate in all aspects of this fundamental research including the synthesis of organic compounds using a series of known procedures, development of new reactions, purification and characterization of products, determination of reaction rates by spectroscopy, and computational studies.