Bromination and dehydrobromination of exocyclic olefin {$8$} resulted in the formation of bromomethylene compound {bf 9} and Wagner-Meerwein rearrangement product ($10$). The dehydrobromination of ($10$} with potassium {it tert}-butoxide provided the corresponding bromomethyl compound ($11$) in high yield. Reaction of ($11$} with Zn-Cu couple in methanol afforded the methyl derivative ($12$} and the parent olefin ($8$}. The unusual formation mechanism of ($ 8$} has been discussed in term of a reductive retro-Wagner-Meerwein rearrangement.