Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents

A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br /BrO3 and I /IO3 reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/Br03 and I /IO3, respectively. Of the two reagents, I /IO3 was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br /BrO3 was effective for vicinal functionalization of traps-stilbene and chalcones. (C) 2009 Elsevier Ltd. All rights reserved.