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 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 64 Issue: 19
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tet.2008.02.067
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.4377-4383

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.