Formation of D-Glucosone as a Chemical Intermediate

In the preparation of D-glucosone by the direct oxidation of D-glucose, D-fructose, or D-mannose by such reagents as that of Fenton,37 cupric acetate,16- 46- 46 selenious acid,16-61 etc., the degree of oxidation must be carefully controlled if the osone, which is the first product, is to be the main product of the reaction. The nature and mechanism of formation of the products of further oxidation of D-glucosone are discussed on p. 68. 

In dilute, alkaline solution, air (or, preferably, oxygen) degrades a sugar 

The reaction mechanism postulated by Wolfrom, Schuetz and Cavalieri87 for the formation of 5-(hydroxymethyl)-2-furaldehyde from D-glucose involves the enol (XXXV) of 3-deoxy-D-glucosone as an intermediate an alternative pathway proposed by these same workers included the enol 

With regard to the formation of levulinic acid by acid treatment of 5-(hydroxymethyl)-2-furaldehyde, Pummerer, Guyot and Birkofer92 pro- 

Neither of these reports has been confirmed, and, in both cases, evidence for the production of D-glucosone is incomplete, being based mainly on the preparation of non-definitive derivatives. These results are discussed more fully in the Section dealing with the biological significance of the osones. 

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