For the Diels-Alder reaction to proceed, the diene should be cis-planar or nearly so. Dienes like biphenyl are not planar due to the o-o’-hydrogen interactions. This interaction increases the activation energy of the reaction. Nitrogen substitution in the ortho position will eliminate the o-o’ interaction, which should lead to a reactant with a lower dihedral angle, and therefore a lower activation barrier for the Diels-Alder reaction. We present the Diels-Alder reactions of ethene and ethyne with a series of nitrogen-substituted bisaryl compounds computed using density functional theory (ωB97X-D/6-311+G(d,p)) in the gas phase.

Nitrogen-substituted bisaryl dienes in the Diels-Alder reaction

253rd National Meeting (2017)

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