Electrocatalytic Achmatowicz Rearrangement Cascade To Construction of Furopyranone

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Efrain Medina Yujie Sun


By Efrain Medina, Chemistry

Advisor: Yujie Sun

Presentation ID: AM_D28

Abstract: The purpose of this project is to create a new method of conducting the Achmatowics rearrangement reaction and create complicated heterocyclic compounds utilizing biomass derivatives. We have developed immobilized transition metal containing molecular electrocatalysts through photo-induced polymerization. Which have shown outstanding performance in the rearrangement reaction. This reaction is important in the development of different pharmaceuticals and the was goal of the project is to create a cleaner and less expensive way of conducting the reaction using only metal catalysts and electricity. Traditionally, to perform this reaction toxic bromine gas is used alongside dilute H2SO4 and we are now displaying a much easier avenue to obtain the same result while avoiding possibly dangerous chemicals. For the project, we used a metal catalyst to test its ability to drive the reaction. A three electrode arrangement was used to perform the experiments to provide the necessary electricity and we were able to also analyze the electrolysis all the way throughout the experiments. The qualitative products were identified with proton NMR (Nuclear Magnetic Resonance) . Also, quantitative yields and Faradaic efficiency were calculated with HPLC (High Performance Liquid Chromatography) by taking aliquots of the electrolyte used in the experiments.

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AM Poster Session -- Great Hall -- D: New Frontiers