SELECTIV BROMINATION OF THE AROMATIC RING IN ω-PHENYLPOLYOXAALKANES AND ALKANOLS IN MICELLES

Article abstract of DOI:10.1016/S0040-4020(01)85934-2

The regioselecticity of bromination of ω-phenylpolyoxaalkanes and alkanols by bromine in aqueous solution of dodecyl sulfate (SDS) and aqueous solution of cetyltrimethylammonium bromide (CTAB) are shown to be related to the average orientation of substrate as indicated by 1H NMR studies.Thus ortho-bromination is promoted at higher concentrations of the surfactant relative to pure water.In contrast, at an equal ratio of the surfactant and substrate para-bromination is promoted.The results are discussed with respect to the average orientation of substrate in a micellar microenvironment and the formation of an ether-bromine comples as possible bromination agent.