High Temperature Isomerization of Benzenoid Polycyclic Aromatic Hydrocarbons. An Analysis through the Bent Bond and Antiperiplanar Hypothesis Orbital Model.
The properties and stereochemical reactivity of cyclobutadiene, benzene, cyclooctatetraene and the [10]- to [14]annulenes can be uniformly rationalized through the bent bond /antiperiplanar hypothesis (BBAH). This new orbital model considers electronic delocalization between pyramidal diradical resonance structures and associated bent bonds, as it applies to aromatic, non-aromatic and anti-aromatic molecules.
BBAH #6: J.-F.Parent, P. Deslongchamps, High Temperature Isomerization of Benzenoid Polycyclic Aromatic Hydrocarbons. An Analysis through the Bent Bond and Antiperiplanar Hypothesis Orbital Model. J. Org. Chem., 2018,83, 3299-3304.
https://doi.org/10.1021/acs.joc.8b00095
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