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.
CEYLAN, MUSTAFA; KINAL, ARMAĞAN; SÜTBEYAZ, YAŞAR; and BALCI, METİN (2003) "Bromination of 1-Cyclopent-1-en-1-ylbenzene and 1-(5-Bromocyclopent-1-en-1-yl)benzene and Theoretical Investigation of the Products," Turkish Journal of Chemistry: Vol. 27: No. 3, Article 2. Available at: https://journals.tubitak.gov.tr/chem/vol27/iss3/2