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Published on: November 15, 2017
Theoretical study of the decomposition of ethyl and ethyl 3-phenyl glycidate
Daniela Josa1, Angeles Peña-Gallego, Jesús Rodríguez-Otero
1Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Universidade de Santiago de Compostela, Rúa Jenaro de la Fuente, s/n, Santiago de Compostela, 15782, Spain.
Abstract:
The mechanism of the decomposition of ethyl and ethyl 3-phenyl glycidate in gas phase was studied by density functional theory (DFT) and MP2 methods. A proposed mechanism for the reaction indicates that the ethyl side of the ester is eliminated as ethylene through a concerted six-membered cyclic transition state, and the unstable intermediate glycidic acid decarboxylates rapidly to give the corresponding aldehyde. Two possible pathways for glycidic acid decarboxylation were studied: one via a five-membered cyclic transition state, and the other via a four-membered cyclic transition state. The results of the calculations indicate that the decarboxylation reaction occurs via a mechanism with five-membered cyclic transition state.
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