Attempted Synthesis of 1-Cyclohepta-1,2-dien-1-ylbenzene and Wurtz-Like Condensation Products in the Reaction of 1-(2,3-Dibromocyclohept-1-en-1-yl)benzene with Zinc

Authors : Mustafa Ceylan, Yakup Budak, M. Burcu Gürdere

Pages : 635-642

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Publication Date : 9999-12-31

Article Type : Makaleler

Abstract :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 1H-and 13C-NMR spectral data) instead of the expected 1-cyclohepta-1,2-dien-1-ylbenzene 14.
Keywords : Substituted strained cyclic allene, dehydrobomination, Wurtz-like condensation, zinc