26306-61-6Relevant articles and documents
Glycosides of N-Hydroxy-N-arylamine Derivatives. Part 3. Kinetic and Mechanistic Studies on the Degradation Reaction of O-Glycosides of N-Hydroxy-N-arylamines and their Acetohydroxamic Acids in Acidic and Alkaline Media
Yoshioka, Tadao,Uematsu, Takayoshi
, p. 1377 - 1382 (2007/10/02)
Good first-order kinetics of the degradation reaction of 1--1-deoxy-β-D-glucopyranoses (1a-d), 1-(N-arylamino)oxy-1-deoxy-β-D-glucopyranose (2a) and sodium 1--1-deoxy-β-D-glucopyranuronate (3a) in aqueous acidic solutions have been observed.Compounds (1a-d) and (3a) were fairly stable in neutral solution, but in aqueous acidic solutions at 20 deg C these compounds decomposed to the corresponding arylamino derivatives (4a-d) and D-gluconic acid (5) .The compound (2a) decomposed ca. 7400 times faster than compound (1a) to the same products (4a) and (5) in the same conditions.In an alkaline solution, compounds (1a)-(3a) gave the corresponding azoxybenzene.In the acid-catalysed redox degradation reaction, the hydrolysis of the N-acetyl group of compounds (1a-d) and (3a) is considered to be the rate-determining step.The effects of pH and additives on the reaction rate are reported.The mechanism of the acid-catalysed redox fission of the N-O linkage in the above O-glycosides is discussed.
