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IV. Summary

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    24635

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    Manganese(III) acetate and ammonium cerium(IV) nitrate react with CH-acidic compounds to produce carbon-centered radicals that add to carbo­hy­drates with electron-rich double bonds. The resulting adduct radicals usually undergo oxidation to produce cations, each of which captures a nucleo­phile and then deprotonates to complete the reaction. Most reported reactions of this type involve the malonyl radical adding to an unsaturated carbohydrate. When the carbohydrate is a gly­cal, this reaction is a regio­specific addition to C-2. Such an addition takes place stereo­selec­tively from the less hindered face of the ring system. Radical addition also occurs to less elec­tron-rich double bonds, but the adduct radical is not oxidized to a cation; instead, it abstracts a hydrogen atom. Manganese(III) acetate also reacts with unsaturated carbohydrates to produce lac­tones.

    This page titled IV. Summary is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Roger W. Binkley and Edith R. Binkley.