Studies Towards the Acceleration of Diels-Alder Reactions using η6-metal Arene Complex Substituents

carrollscholars.object.degreeBachelor's
carrollscholars.object.departmentChemistry and Physics
carrollscholars.object.seasonSpring
dc.contributor.advisorHitt, David
dc.contributor.advisorRowley, John
dc.contributor.advisorBeck, Ashley
dc.contributor.authorLohar, Noah
dc.date.accessioned2024-05-28T20:16:08Z
dc.date.available2024-05-28T20:16:08Z
dc.date.issued2024
dc.description.abstractThe Diels-Alder (DA) reaction is a cycloaddition reaction between a conjugated diene and a two-atom π system (dienophile) that forms an unsaturated six-membered ring. DA reactions under normal electron-demand conditions (diene is electron rich) are limited by the dienophile requiring an electron-withdrawing group (EWG) to proceed at a reasonable rate. These EWGs, in short, are functional groups conjugated with the π system that can act as π acceptors, most commonly nitriles, carbonyl functional groups (e.g. ketones,esters, etc.), and nitro groups. The complexation of a monocationic (𝜂5-cyclopentadienyl)metal fragment (CpM+) to the π system of a benzenoid compound in an 𝜂6 configuration results in significant electron withdrawal from substituents attached to the aryl ring. This functionality, therefore, may expand the applicability of the Diels-Alder reaction to progress by utilizing the CpM(𝜂6-aryl) substituent as activating dienophile substituents. Towards this goal, we have isolated the DA adduct between CpRu(η6-ethyl trans-cinnamate)PF6 and 2,3-dimethyl-1,3-butadiene. Characterization of the adduct has been assigned on the basis of 1H NMR, 13C NMR, and IR spectra. This research also explored the synthesis of an analogous iron complex, CpFe(η6-ethyl trans-cinnamate)PF6, to accelerate DA reactions. Compared to ruthenium, iron offers many advantages primarily due to its abundance compared to ruthenium. Herein, we report our progress in synthesizing CpFe(η6-ethyl trans-cinnamate)PF6.
dc.identifier.urihttps://hdl.handle.net/20.500.12647/10908
dc.language.isoen_US
dc.titleStudies Towards the Acceleration of Diels-Alder Reactions using η6-metal Arene Complex Substituents
dc.typeThesis
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