Reactions at position 1 of carbohydrates. Part IX. A reinvestigation of the bond cleavage in the acid-catalysed hydrolysis of ferrocenylmethyl β-D-glucopyranoside

Abstract
The acid-catalysed hydrolysis of ferrocenylmethyl β-D-glucopyranoside in H2 18O has been reinvestigated. Contrary to an earlier report, the glucose formed contained no 18O isotopic enrichment. This shows that cleavage of the bond between the oxygen and aglycon–carbon occurred during the hydrolysis. Acid-catalysed methanolysis of ferrocenylmethyl β-D-glucopyranoside gave glucose and methoxymethylferrocene. Consequently bond cleavage occurred at the same position in both reactions.

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