Electrophilic Substitution of Aromatic Compounds by Unsaturated Sugar Derivatives

Abstract

Hexenopyranosyl Carbocations, Pent-2-enopyranos-4-ulosyl Carbocations Glycals 1 and 2 react with methoxybenzene in the presence of SnCLj forming ^-substi-tuted C-glycosyl compounds 4 and 5 + 6 respectively. Under similar conditions 1-O-benzoyl-or methyl pent-2-enopyranos-4-uloses (7) and (8) react with electron rich aromatic compounds furnishing either C-glycosyl compounds or C-2 aryl substituted products depending on the nature of the aromatic component as well as the kind of substituent at C-1.