New polyhalogenated benzobarrelenes were synthesized in good yields. The bromination reaction of benzobarrelenes at high temperature gives non-rearranged products. Dehydrobromination of the formed products with t-BuOK yielded the desired polyhalogenated benzobarrelenes. The elimination reaction of cyclopropanoid dibromide with a base unusually resulted in the formation of a benzosemibullvalene derivative. © 2009 Elsevier Ltd. All rights reserved.
Şengül, M. E., Gültekin, D. D., Eşsiz, S., Şahin, E., & Daştan, A. (2009). The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative. Tetrahedron, 65(25), 4859–4865. https://doi.org/10.1016/j.tet.2009.04.034