The first and efficient synthesis of some of the polyhalogenated benzobarrelenes: unusual formation of a benzosemibullvalene derivative

ŞENGÜL M., Gültekin D. D., Eşsiz S., ŞAHİN E., DAŞTAN A.

Tetrahedron, vol.65, no.25, pp.4859-4865, 2009 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 65 Issue: 25
  • Publication Date: 2009
  • Doi Number: 10.1016/j.tet.2009.04.034
  • Journal Name: Tetrahedron
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4859-4865
  • Keywords: Benzobarrelene, Benzosemibullvalene, Bromination, Polybromides, Polychlorides, Polyhalogenides
  • Hakkari University Affiliated: No


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.