Reactivity of glucosyl radical in the presence of phenols

Glucosyl radicals from the photoreaction of α-bromo-2,3,4,6-tetra- O -acetylglucose ( ABG ) with hexabutylditin react with phenols. 4-H 3 COC 6 H 4 O• was identified by means of EPR spectroscopy in the case of 4-methoxyphenol, and the corresponding α - 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 α - O -glucosides observed in the electrochemical reaction of ABG and phenols, although in this case the dimers represent the main reaction products.