Bromination of 1-cyclopent-1-en-1-ylbenzene and 1-(5-bromocyclopent-1-en-1-yl)benzene and theoretical investigation of the products

Ceylan M., Kinal A., Sutbeyaz Y., Balci M.

TURKISH JOURNAL OF CHEMISTRY, vol.27, no.3, pp.287-294, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 3
  • Publication Date: 2003
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.287-294
  • Middle East Technical University Affiliated: No

Abstract

The bromination of 1-cyclopent-1-en-1-ylbenzene (4) in different solvents and at different temperatures was accompanied by the evolution of hydrogen bromide and yielded 1-(5-bromocyclopent-1-en-1-yl)benzene (8). Further bromination of 8 gave exclusively 2R(S),5R(S)-1-(1,2,5-tribromocyclopentyl) benzene (11). The experimental results were compared with the theoretical ones based on semi-empirical (MM+ and AM1), Hartree-Fock (HF) and density functional theory (DFT). The formation of 11 was explained by the formation of a weakly bridged bromoniun ion of type 9.