A new, comprehensive insight on the competition between (4+2) and (2+4) cycloaddition schemes and molecular mechanism of Diels-Alder reaction of 2-nitrofuran with isoprene

Key Points

• This study aims to clarify the mechanisms and competition between [4+2] and [2+4] cycloadditions in Diels-Alder reactions involving 2-nitrofuran and isoprene.
• Employing Molecular Electron Density Theory at the ωB97XD/6-311G(d,p) level of theory.
• Analyzing the reactivity of 2-nitrofuran with isoprene through computational methods.
• Investigating the competing mechanistic pathways for cycloaddition.
• Identified significant differences in reaction pathways between the two cycloaddition schemes.
• Provided detailed energy profiles for both [4+2] and [2+4] pathways.
• Reactivity analysis suggested the predominance of the [4+2] mode under examined conditions.