Carbohydrate Research p. 89 - 94 (1983)
Update date:2022-08-03
Topics:
Williams, Michael J.
N.m.r. spectroscopy (13C and 1H) has been used to show that saccharide hydrazones in solution in hydrazine exist mainly as the syn acyclic-tautomer.In deoterium oxide solutions, slow tautomerisation occours to give glycosylhydrazines; at pH 6 tautomerism is rapid and the latter preponderate; exceptions are the hydrazones of D-ribose and L-arabinose which give almost equal proportions of acyclic and cyclic tautomers at pH 6.Reaction of representative saccharide hidrazones with nitrous acid gives a mixture of the corresponding saccharide and the β-glycosyl azide, the latter being formed from the glycosylhydrazine tautomer.
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