The reaction of 1,2-halohydrins derived from easily available carbohydrates with (diacetoxyiodo)benzene (DIB) in the presence of bromine is a mild procedure for the synthesis of 1-deoxy-1-halo-1-bromo-alditols with one carbon less than the original carbohydrate. The reaction goes through β-fragmentation of the intermediate anomeric alkoxyl radicals. These 1-halo-1-bromo polyhydroxy compounds may be valuable synthetic intermediates in organic synthesis.
- radical reactions
Gonzalez, C. C., Kennedy, A. R., Leon, E. I., Riesco-Fagundo, C., & Suarez, E. (2001). Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds. Angewandte Chemie, 40(12), 2326-2331. https://doi.org/10.1002/1521-3773