RUI: Effects of Cationic Substituents on the Cope Rearrangement

Xavier University Of Louisiana, New Orleans LA

Investigators

Abstract

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.