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Magnus Carlsson, Johan Lind, Gábor Merényi

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

Keywords: carbohydrate, carbonate radical, glucosidic cleavage, hydrogen abstraction, intramolecular, model compounds, selectivity

In the presence of oxygen, radiolytically generated carbonate radical anions, CO₃^?–, were reacted with methyl ?-D-cellobioside and methyl ?-D-glucoside. From the ensuing product pattern, it was concluded that CO₃^?– 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 CO₃^?– 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 CO₃^?– as a bleaching agent for pulp.

Holzforschung, Walter de Gruyter

Print ISSN: 0018-3830
Volume: 60, 03/2006
Pages: 130 - 136

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