Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono-and dibromide derivatives: Unexpected Wagner-Meerwein rearrangement on silica gel

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Turkish Journal of Chemistry, vol.35, no.4, pp.587-598, 2011 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 35 Issue: 4
  • Publication Date: 2011
  • Doi Number: 10.3906/kim-1101-991
  • Journal Name: Turkish Journal of Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.587-598
  • Keywords: Benzobarrelene, Bromination, Wagner-Meerwein rearrangement
  • Hakkari University Affiliated: No


The bromination reaction of dihydrobenzobarrelene under different conditions was studied. The bromination reaction of dihydrobenzobarrelene with molecular bromine gave only a Wagner-Meerwein rearrangement product by aryl and alkyl migration. Its high-temperature bromination reaction resulted in the formation of normal addition products besides rearrangement products. The bromination reaction of the alkene with 1,2-dibromotetrachloroethane (DBTCE) gave a non-rearrangement product as the sole product. The synthesis and bromination reaction of 2-bromodihydrobenzobarrelene was also studied. An unexpected Wagner-Meerwein rearrangement was observed on silica gel during the column chromatography of isomeric tribromides. Herein, we report the results of the synthesis, and the X-ray crystal structures and the possible mechanism of processes are discussed. © TÜBITAK.