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Abstract:
To explore the applicability of highly active metal-graphite reducing agents to polyfunctional compounds a variety of suitably protected chloro-, bromodeoxy- and deoxyiodohexopyranosides and hexofuranoses were each treated with potassium-graphite laminate (C8K) and zinc/silver-graphite, respectively, invariably leading to the efficient formation of olefinic products. However, while C8K in all cases causes dehydrohalogenation, zinc/silver-graphite reductions proceeded by dealkoxyhalogenation, results quite opposite to the formation of glycals by each of the reagents. In contrast, magnesium on graphite readily dimerizes Me 6-deoxy-6-iodo-α-D-glucopyranoside by a Wurtz reaction.
