Abstract
This chapter discusses two extensions of carbohydrate chemistry into organic fields—namely, the applications of the Friedel-Crafts and Grignard reactions to carbohydrate starting materials. The isolation from the Grignard glucosylation of benzene of a product identical with that obtained by the Friedel-Crafts method have made it apparent that no intramolecular isomerizations or inversions accompany the process, and that the products possess the configuration of their parent aldose. Various applications––formation of molecular addition compounds, carbonyl addition reactions and metathetical reactions––of the Grignard reaction are discussed. D -fructose pentaacetate, tetraacetyl- D -glucose, and methyl tetraacetyl-α- D -glucoside give precipitates with methylmagnesium iodide, all analyzing as adducts containing two moles of Grignard reagent. No evidence of stable complex formation is noted; the only reaction found is the normal one of Grignard reagents with esters.
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