- Fischer found that if one molecule of phenylhydrazine acted upon one molecule of an aldose or ketose a hydrazone resulted which in most cases was very soluble in water, but if three molecules of the hydrazine reacted (one of which is reduced to ammonia and aniline) insoluble crystalline substances resulted, termed osazones, which readily characterized the sugar from which it was obtained.
The identity of the formulae and osazones of d-mannose and d-glucose showed that the stereochemical differences were situated at the carbon atom adjacent to the aldehyde group. Fischer applied a method indicated by Pasteur in converting dextro into laevo-tartaric acid; he found that both d-mannonic and d-gluconic acids (the latter is yielded by glucose on oxidation) were mutually convertible by heating with quinoline under pressure at 140°.
Cane sugar has no reducing power and does not form an hydrazone or osazone; the other varieties, however, reduce Fehling's solution and form hydrazones and osazones, behaving as aldoses, i.e.
The osotriazoles are obtained by heating the osazones of orthodiketones with mineral acids; by the action of acetic anhydride on the hydrazoximes of orthodiketones, or by condensing diazo-methane with cyanogen derivatives (A.