The thermal rearrangements of naphthalene and azulene. An analysis through the bent bond and antiperiplanar hypothesis orbital model
The thermal conversion of azulene, naphthalene, norcaradiene, and polycyclic analogues can be rationalized through the Bent Bond/Antiperiplanar Hypothesis (BBAH) orbital model. The BBAH postulates that higher-energy pyramidal singlet diradical intermediates can be used to rationalize molecular rearrangements of these benzenoid aromatics under thermal conditions.
BBAH #13: P. Deslongchamps, The thermal rearrangements of naphthalene and azulene. An analysis through the bent bond and antiperiplanar hypothesis orbital model, Tetrahedron, 2021, 82, 131956-131969.
https://doi.org/10.1016/j.tet.2021.131956
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