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The behaviour of d-fructose and inulin towards anhydrous hydrogen fluoride

✍ Scribed by Jacques Defaye; Andrée Gadelle; Christian Pedersen


Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
950 KB
Volume
136
Category
Article
ISSN
0008-6215

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✦ Synopsis


Inulin and D-fructose are quantitatively converted into a mixture of Mructose dianhydrides on treatment with anhydrous hydrogen fluoride. Of the six dianhyd~des isolated, five are known compounds, whereas one, P_Mructofuranose @-r>-fructopyranose 2,1':3,2'-dianhydride, has not been described hitherto. The structures of two of the known dianhydrides have been revised. The relative amounts of dianhydrides obtained depend on the reaction conditions. The reaction of D-fructose with hydrogen fluoride is shown, using 13C-n.m.r. spectroscopy, to involve ~-~u~tofuranosyl fluoride as a probable intermediate. Dianhydrides are also formed when D-fructose is treated with methanol and sulfuric acid under Fischer glycosidation conditions or with trifluoroacetic acid.


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