4164 
By way of a simple example first of all the action of sodium 
hypochlorite on the amide of mandelic acid was investigated. This 
readily gives benzaldehyde. As the amide is insoluble in water a 
methylaleoholic solution was employed. That in this reaction an 
intramolecular atom-rearrangement analogous to that in Hormann’s 
reaction takes place, was shown by the fact that on adding hydrazine- 
sulfate to the reaction liquid and neutralizing it there was formed 
benzalazine, benzalsemicarbazone and also a little azodicarbonamide, 
which could be readily separated with ether and alcohol. 
From the appearance of the two last named compounds it necessarily 
follows that in the reaction sodium isocyanate is formed. 
The course of the reaction may, therefore, be represented as follows: 
CH, Cr — CQ, + NaOCl->C,H,Cou—C° Nna—> CU, H,Con—N=C=0 
CHC — N= C= 0 + NaOH => C,H,C5 + NaNCO 
NH, 
Jl | Zl 
NaNCO + NH, .NH,. H,SO, CO 
NH — NH, 
NH — NH, 
Tl 
NaNCO +2. NH, .NH,. H,S0, CO 
A 
NH — NH, 
In the ease of these a-oxyacids the halogen amide cannot be 
isolated beeause the reaction takes place momentarily. The reaction 
is further distinguished from that in the saturated and unsaturated 
acid amides in so far that in the latter are formed from the isocyanic. 
esters carbaminic salts or urethanes, whereas here with the a-oxy- 
acids the isocyanate group is split off as such. 
After the course of the reaction had been ascertained for mandel- 
amide, it was applied to amides of acids formed on oxidation of 
sugars and in this manner was obtained a new method for the 
degradation of sugars. 
Degradation of d-glucose. 
The course of the reaction was represented by the following scheme: 
