Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes

GUELTEKIN D., TAŞKESENLİGİL Y., DAŞTAN A., Balci M.

TETRAHEDRON, cilt.64, sa.19, ss.4377-4383, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 64 Sayı: 19
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1016/j.tet.2008.02.067
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.4377-4383
  • Anahtar Kelimeler: norbornene, non-classical carbocation, bromination, Wagner-Meerwein rearrangement, gamma-gauche effect, HIGH-TEMPERATURE BROMINATION, MAGNETIC-RESONANCE SPECTRUM, ELECTROPHILIC BROMINATION, PROTONATED NORTRICYCLENE, CONVENIENT SYNTHESIS, EXO ATTACK, BENZONORBORNADIENE, ENDO, IONS, 2,3-DIBROMOBENZOBARRELENE
  • Atatürk Üniversitesi Adresli: Evet

Özet

The low and high temperature bromination of 7-bromobicyclo[2.2.1]hept-2-ene and 2,7-dibromobicyclo[2.2.1]hept-2-ene were studied and the possible role of a neighboring group participation in rearrangements was investigated. The formation mechanism of the isomers as well as the role of the substituent on the rearrangement were discussed. The structure elucidation of the formed compounds was achieved by NMR spectral data; particularly, the gamma-gauche effect was discussed in connection with the configuration of the bromine atoms. (c) 2008 Elsevier Ltd. All rights reserved.