There are multiple accounts in the literature of the reaction between diethyl succinate and potassium tert-butoxide, but unlike other conjugated, nonaromatic tautomeric systems, we observe only the enol tautomer regardless of solvent conditions. Additionally, we find no spectroscopic or crystallographic data suggesting formation of the keto isomer in the literature. The di-enol form of diethyl succinylsuccinate is crystalline and displays thermodynamic stability both in experimental and computational models. We characterized the Claisen condensation products of both diethyl and dimethyl esters of succinic acid spectroscopically in an effort to better understand this system. The goal of our research is to experimentally verify reproducible reaction results, compare the results achieved under different reaction conditions, and characterize this equilibrium using both experimental and computational methods.

Investigation of the microwave-assisted claisen condensation of diethyl succinate

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.