HIGH-TEMPERATURE BROMINATION .5. FUNCTIONALIZATION OF BENZONORBORNADIENE - HIGH-TEMPERATURE BROMINATION AND ELECTROCHEMICAL OXIDATION

DASTAN A., DEMIR Ü., BALCI M.

JOURNAL OF ORGANIC CHEMISTRY, cilt.59, sa.22, ss.6534-6538, 1994 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 59 Sayı: 22
  • Basım Tarihi: 1994
  • Doi Numarası: 10.1021/jo00101a011
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6534-6538
  • Atatürk Üniversitesi Adresli: Evet

Özet

The electrophilic addition of bromine to benzonorbornadiene (1) at 10 degrees C led in high yield to the formation of 2-exo-7-anti-dibromide 2. However, high-temperature bromination in decalin at 150 degrees C resulted in the formation of five products, 2-6, consisting of non-rearranged and rearranged products in a ratio of 8:2. Conducting the bromination reaction in the presence of a free radical inhibitor like 2,4,6-tri-tert-butylphenol suppressed the formation of the non-rearranged products. This very strongly supports the assumption that there is a competition between radical and ionic reactions. Anodic oxidation of benzonorbornadiene was investigated. Electrolysis of benzonorbornadiene in different solvents resulted in the formation of 2,7-disubstituted benzonorborn-5-ene derivatives, 8-11, in good yields.