We report an experimental and computational investigation of the likely mechanism of a cascade reaction. The reaction involves an intramolecular Diels–Alder reaction, followed by a C–C bond cleavage, to afford a complex bridged bicyclic product. As multiple reaction pathways could be envisioned for the latter step, the mechanism of the C–C bond cleavage step was investigated. Two reasonable reaction pathways were evaluated. Both computations and experiments indicate that the C–C bond cleavage step proceeds by a retro-carbonyl-ene pathway rather than a retro-aldol pathway. This report underscores the synergy between computational and experimental studies and establishes the mechanism of an interesting complexity-generating transformation.
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Bulger et al. (2024) studied this question.
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