Glucose phenyl hydrazone

CH2OH Glucose, Aldo-hexose CH20H Glucose phenyl hydrazone... 

CH20H Glucose phenyl hydrazone 1 CH20H Oxidation product... 

On this glucose phenyl hydrazone the phenyl hydrazine acts as an oxidizer and one of the secondary alcohol groups (—CH—OH—) is oxidized to a ketone carbonyl group, the phenyl hydrazine being reduced as above to aniline and ammonia. 

The formazan values of the three modifications of D-glucose phenyl-hydrazone (each with a different melting point) observed during muta-... 

The reaction of glucose with an excess of phenylhydrazine (phenyl-diazane) is particularly noteworthy because two phenylhydrazine molecules are incorporated into one of glucose. Subsequent to the expected phenyl-hydrazone formation, and in a manner that is not entirely clear, the —CHOH— group adjacent to the original aldehyde function is oxidized to a carbonyl group, which then consumes more phenylhydrazine to form a crystalline derivative called an osazone, or specifically glucose phenylosazone ... 

Osazones. Glucosazone.— This intermediate product, the oxidation compound, containing, now, a new carbonyl group, reacts with a third molecule of phenyl hydrazine forming a double phenyl hydrazone which is known as an osazone. From glucose the osazone is known as glucosazone. 

This same reduction of phenyl hydrazine occurs when it acts as an oxidizing agent upon the hydrazone formed by the reaction between glucose and phenyl hydrazine. 

Osotriazoles of diketones previously had been described by von Pech-mann 2 0) who obtained them by the oxidation of the corresponding di-hydrazones. The corresponding osotriazoles of the sugars are formed directly by the action of copper sulfate. The formation of the phenyl-D-glucoso-triazole (II) from glucose phenylosazone (I) is illustrated. Its structure is demonstrated by oxidation with periodic acid to the 2-phenyl-4-formyl-osotriazole (III) which is identical with the product obtained previously by von Pechmann from mono-0-acetyldinitrosoacetone phenylhydrazone (IV). 

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