Alkene oxidation using sodium hypochlorite

Abstract

Oxidative halogenation of 1-hexene, 1, 5-hexadiene, cyclohexene and methylmethacrylate using sodium hypochlorite, acetic acid and sodium bromide combination were carried out. Without bromide, dichlorocompounds were obtained. In the presence of excess bromide (10-fold excess), dibromocompounds were obtained exclusively. However, the amount of bromide between 1-5 fold excess gave a mixture of dihalocompounds. Co-solvents such as hexane and isooctane did not improve yield of the products. Moreover, the presence of co-solvent gave a mixture of products including haloalcohol as evidence by NMR spectroscopy and MS spectroscopy. The mechanism of this reaction was proposed to involve halonium ions intermediate.