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

DOI

-

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 ^{13}C-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

First Page

635

Last Page

642

Recommended Citation

CEYLAN, MUSTAFA; BUDAK, YAKUP; and GÜRDERE, M. BURCU (2006) "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," Turkish Journal of Chemistry: Vol. 30: No. 5, Article 11. Available at: https://journals.tubitak.gov.tr/chem/vol30/iss5/11