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

MK Agrawal, S Adimurthy, B Ganguly, PK Ghosh

Index: Agrawal, Manoj K.; Adimurthy, Subbarayappa; Ganguly, Bishwajit; Ghosh, Pushpito K. Tetrahedron, 2009 , vol. 65, # 14 p. 2791 - 2797

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Citation Number: 40

Abstract

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−/BrO3− and I−/IO3−, respectively. Of the two reagents, I−/IO3− was established to be the preferred reagent for vicinal functionalization ...