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Readily accessible, oxygenated 6,6‐dibromobicyclo[3.1.0]hexanes react with isovanillin in the presence of silver salts and an inorganic base to afford ring‐expanded/nucleophilic trapping products of various regio‐ and stereo‐chemical forms. Most such products undergo efficient, intramolecular Mizoroki‐Heck reactions to give the corresponding tetrahydrodibenzofurans. In certain cases, simple variations...