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RESEARCH PRODUCT
Why do Electron-Deficient Dienes React Rapidly in Diels?Alder Reactions with Electron-Deficient Ethylenes? A Density Functional Theory Analysis
Luis R. Domingosubject
chemistry.chemical_compoundReaction mechanismDieneNucleophileChemistryElectrophilic additionComputational chemistryOrganic ChemistryElectrophileDensity functional theoryPhysical and Theoretical ChemistryElectron deficiencyCycloadditiondescription
The Diels−Alder reaction of the electron-deficient (ED) dimethyl 2,3-dimethylenesuccinate with two electron-rich (ER) and two ED ethylenes has been studied at the B3LYP/6-31G* level of theory. The analysis of the geometry and electronic structure of the transition state of the reaction with the ED dimethyl 2-methylenemalonate along with the analysis of the global and local electrophilicity indices of the reagents provide an explanation of the participation of this ED diene as nucleophile against powerful electrophiles in polar Diels−Alder reactions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-12-01 | European Journal of Organic Chemistry |