Synthesis of a Model CpFe(eta-6 -aryl) Substituted Dienophile
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Authors
Montowski, Claire
Date of Issue
2023-04-28
Type
Presentation
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Abstract
Diels-Alder (DA) reactions occur between two molecules, a diene and a dienophile, to form a six-membered ring. This structure is commonly found in natural products making it synthetically useful and causing the reaction to commonly be used in the formation of many pharmaceuticals and agrochemicals. However, under most circumstances, the DA reaction is limited by the dienophile needing an electron-withdrawing group to progress at a reasonable reaction rate. While there are numerous electron-withdrawing groups, most require chemical modification to be removed after the reaction. One possible alternative would be to use a dienophile containing an aryl substituent complexed to a (cyclopentadienyl)iron (II) monocationic fragment. This causes the attached 6-carbon ring to become electron-withdrawing, which would extend to the dienophile π-system as well. Furthermore, the metal fragment can later be removed by photolysis upon completion of the DA reaction. Previous research conducted with an analogous ruthenium complex displayed the metal fragment’s ability to accelerate the DA reaction compared to a control experiment with a non-metallated dienophile. The iron complex, by comparison, should have similar properties to the ruthenium complex based on its similar periodic properties and has the added benefit of being much less expensive and easier to remove photolytically. We will report our progress on synthesizing a model CpFe(η6 -aryl) substituted dienophile and on resulting studies into its reactivity in a DA reaction.