The Bent Bond / Antiperiplanar Hypothesis and the Chemical Reactivity of Annulenes.
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 #11: G. Deslongchamps, P. Deslongchamps, The Bent Bond / Antiperiplanar Hypothesis and the Chemical Reactivity of Annulenes, J. Org. Chem., 2020, 85, 8645-8655.
https://doi.org/10.1021/acs.joc.0c01069
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