A new mechanism for the thermal and photochemical Diels-Alder cycloaddition based on the bent bond/antiperiplanar hypothesis orbital model
The thermal and photochemical stereochemical reactivity of norbornene derivatives (Diels-Alder, retro- Diels-Alder, Cope rearrangement) can be rationalized through the Bent Bond /Antiperiplanar Hypothesis (BBAH) orbital model at the molecular level. This new orbital model considers unsaturations as Pauling τbonds and electronic delocalization is expressed through pyramidal radical resonance structures inter- acting in antiperiplanar fashion with the antibonding orbital of τ bonds.
BBAH #18: P. Deslongchamps, A new mechanism for the thermal and photochemical Diels-Alder cycloaddition based on the bent bond / antiperiplanar hypothesis orbital model, J. Mol. Struct, 2022, 1264, 133288-133305.
https://doi.org/10.1016/j.molstruc.2022.133288
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