6533b823fe1ef96bd127f4a0

RESEARCH PRODUCT

A DFT study of the polar Diels–Alder reaction between 4-aza-6-nitrobenzofuroxan and cyclopentadiene

Luis R. DomingoM. T. PicherFrançois TerrierPau Arroyo

subject

Reaction mechanismCyclopentadieneChemistryOrganic ChemistrySigmatropic reactionBiochemistryAdductchemistry.chemical_compoundComputational chemistryReagentDrug DiscoveryElectrophilePolarDiels–Alder reaction

description

Abstract The polar Diels–Alder reaction between 4-aza-6-nitrobenzofuroxan (ANBF) and cyclopentadiene has been studied using DFT procedures at the B3LYP/6-31G* level. Only one highly asynchronous transition state structure associated to the formation of the [4+2] adduct 13 is found. A further [3,3] sigmatropic shift on the [4+2] cycloadduct 13 allows its conversion into the thermodynamically more stable [2+4] cycloadduct 14 . The analysis of the global and local electrophilicities of the reagents correctly explain the behaviour of ANBF as a strong electrophile in polar cycloadditions.

yearjournalcountryeditionlanguage
2005-08-01Tetrahedron
https://doi.org/10.1016/j.tet.2005.05.080