Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes

Gueltekin D. D., TAŞKESENLİGİL Y., DAŞTAN A., BALCI M.

TETRAHEDRON, vol.64, no.19, pp.4377-4383, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 64 Issue: 19
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tet.2008.02.067
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4377-4383
  • Keywords: 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
  • Middle East Technical University Affiliated: No

Abstract

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.