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In the presence of oxygen, radiolytically generated carbonate radical anions, CO 3  •– , were reacted with methyl β-D-cellobioside and methyl β-D-glucoside. From the ensuing product pattern, it was concluded that CO 3  •–  abstracts hydrogen atoms predominantly from glucosidic C1–H bonds. This high intramolecular selectivity was rationalised mainly in terms of a polar effect on the transition state of the hydrogen abstraction reaction. The present findings are in sharp contrast to the relative inertness of CO 3  •–  towards glucosidic C1–H bonds previously observed in cotton linters. The reasons for this discrepancy are discussed in light of a possible future role of CO 3  •–  as a bleaching agent for pulp.

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A selectivity study of reaction of the carbonate radical anion with methyl β- d -cellobioside and methyl β- d -glucoside in oxygenated aqueous solutions