Reactivity of glucosyl radical in the presence of phenols

Glucosyl radicals from the photoreaction of a-bromo-tetra-O-acetylglucose (ABG) with hexabutylditin react with phenols. 4-H3COC6H4O. was identyified by means of EPR spectroscopy in the case of 4-methoxyphenol, and the corresponding a-O-glucoside was isolated along with 1- and 2-deoxysugars and the dimers of glucosyl radical. The present results are consistent with the formation of a-O-glucosides observed in the electrochemical reaction of ABG and phenols, although in this case the dimers represent the main reaction products.