Abstract
A novel method for the generation of o-quinodimethane (o-QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[c]oxepines. Among the benzo[c]oxepines studied, indanone containing analogues demonstrated the greatest variety of reactivity. A number of decay modes were observed, in addition with trapping of the o-QDM intermediates using dienophiles for the synthesis of polysubstituted tetrahydronaphthalenes with high regioselectivity. This research provided a novel method to generate o-QDM intermediates from benzo[c]oxepine precursors.
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