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

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

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

carbohydrate

carbonate radical

glucosidic cleavage

hydrogen abstraction

intramolecular

model compounds

selectivity

Chemistry

Kemi

Publication and Content Type

ref (subject category)

art (subject category)