RT Journal Article
T1 Understanding the reactivity and selectivity of Diels–Alder reactions involving furans
A1 Alves, Tiago Vinicius
A1 Fernández López, Israel
AB The reactivity and endo/exo selectivity of the Diels–Alder cycloaddition reactions involving furan and substituted furans as dienes have been computationally explored. In comparison to cyclopentadiene, it is found that furan is comparatively less reactive and also less endo-selective in the reaction with maleic anhydride as the dienophile. Despite that, both the reactivity and the selectivity can be successfully modified by the presence of substituents at either 2- or 3-positions of the heterocycle. In this sense, it is found that the presence of strong electron-donor groups significantly increases the reactivity of the system while the opposite is found in the presence of electron-withdrawing groups.The observed trends in both the reactivity and selectivity are analyzed quantitatively in detail by means of the activation strain model of reactivity in combination with the energy decomposition analysis methods.
PB Royal Society of Chemistry
SN 1477-0520
SN 1477-0539
YR 2023
FD 2023
LK https://hdl.handle.net/20.500.14352/105805
UL https://hdl.handle.net/20.500.14352/105805
LA eng
NO T. V. Alves and I. Fernández, Org. Biomol. Chem., 2023, 21, 7767-7775
DS Docta Complutense
RD 20 ene 2026