The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from alpha-Tropolone O-Methyl Ether and Trimethylenemethane

The title bicyclic system 3, the adduct arising from the formal [6+3] cycloaddition of α‐tropolone O‐methyl ether (1) and trimethylenemethane (2), has been prepared and subject to single‐crystal X‐ray analysis. The chemical manipulation of adduct 3 in a range of ways is reported, including through acid‐catalysed rearrangement of the derived mono‐oxide to give the bicyclo[4.3.1]undecane 21.We thank the Australian Research Council and the Institute of Advanced Studies for financial support. MLC acknowledges an ARC Laureate Fellowship, support from the ARC Centre of Excellence for Electromaterials Science and generous allocations of supercomputing time on the National Facility of the Australian National Computational Infrastruct