Bromination of endo- and exo-benzocyclobutenonorbornene derivatives: neighbour group effect on bromination

UZUNDUMLU E., Dastan A.

JOURNAL OF CHEMICAL RESEARCH-S, sa.6, ss.348-351, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2005
  • Dergi Adı: JOURNAL OF CHEMICAL RESEARCH-S
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.348-351
  • Atatürk Üniversitesi Adresli: Evet

Özet

The electrophilic addition of bromine to 13-anti-bromo-endo-benzocyclobutenonorbornene 7 at-50 +/- 5 degrees C has led in high yield to the formation of the rearranged dibromides 9, 10 and 11. In addition to this, bromination of exo isomer 8 results in formation of rearranged 9 and non rearranged product 10. However, high-temperature bromination of endo 7 and exo isomer 8 at 77 degrees C gave only non-rearranged products. The possible role of a substituent in rearrangements is discussed in these systems.