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 H₂¹⁸O 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.