RT Book,_Section
T1 Theoretical study of the mechanisms of the decomposition of ethyl and ethyl 3-phenyl glycidate
A1 Josa, Daniela
A1 Peña Gallego, María de los Ángeles
A1 Rodríguez Otero, Jesús
A1 Cabaleiro Lago, Enrique Manuel
K1 Ethyl glycidate
K1 Ehyl 3-phenyl glycidate
K1 Ab initio calculations
K1 Reaction mechanism
AB One of the most important transformations of glycidic esters is their decarboxylation to give rise to aldehydes and ketones. A proposed mechanism for the decomposition of the ethyl 3-phenyl glycidate 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 rapidly decarboxylates to give the corresponding aldehyde. Two possible pathways for the glycidic acid decarboxylation were proposed, one of them via a five-membered cyclic transition state and the other one via a four-membered cyclic transition state(Chuchani, G.; Tosta, M.; Rotinov, A.; Herize, A. J. Phys. Org. Chem. 2004, 17, 694). An accurate experimental description of the glycidic acid decarboxylation is a challenging task, since the glycidic acids decompose even at room temperature. Therefore, the goal of this work is investigated the path more favored by decarboxylation. Theoretical calculations were carried out in order to probe this proposed mechanism. Geometries of the different reactants, products and intermediates were optimized at different levels of calculation. The vibrational frequencies were calculated at the same level. The results were compared with those from experiments. Theoretical calculations indicate that the glycidic acid decarboxylation occurs via a five-membered cyclic transition state
PB MDPI
SN 3-906980-25-1
YR 2011
FD 2011
LK http://hdl.handle.net/10347/26900
UL http://hdl.handle.net/10347/26900
LA eng
NO Proceedings of the 15th International Electronic Conference on Synthetic Organic Chemistry, 1–30 November 2011, MDPI: Basel, Switzerland, doi:10.3390/ecsoc-15-00672
NO The 15th International Electronic Conference on Synthetic Organic Chemistry session Computational Chemistry
NO D. J. thanks the Spanish Ministry of Education for FPU scholarship
DS Minerva
RD 24 abr 2026