7,7-Dibromo-1-phenylbicyclo[4.1.0]heptane 4 was synthesized and its thermal and silver ion-catalyzed rearrangements were studied. Alcohol 8 was converted to 1-(2,3-dibromocyclohept-1-en-1-yl) benzene 6. The zinc-mediated elimination of 1- (2,3-dibromocyclohept-1-en-1-yl) benzene 6 resulted in the formation of 2 isomeric Wurtz-like condensation products 15 and 16 (whose structural assignments were based on H-1-and C-13-NMR spectral data) instead of the expected 1-cyclohepta-1,2-dien-1-ylbenzene 14.