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

Essiz S., SENGUL M. E., ŞAHİN E., DAŞTAN A.

TURKISH JOURNAL OF CHEMISTRY, cilt.35, sa.4, ss.587-598, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 35 Sayı: 4
  • Basım Tarihi: 2011
  • Doi Numarası: 10.3906/kim-1101-991
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.587-598
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.