Mr Fenton, Oxidation in Presence of Iron. 
365 
other properties with (3-acrosazone (Fenton and Jackson, B. A. 
Report, 1899). Later, Jackson {Trans. Chem. Soc. 1900. 129) 
by similar treatment found also an osazone closely resembling 
a-acrosazone. 
It is not improbable that glycollic aldehyde may be produced 
as an intermediate stage in the formation of ‘formose’ from 
formaldehyde, and that the two condensation products may be 
identical ; this suggestion is supported by the fact that Pechmann 
(. Ber . 1897. 2459) has obtained glyoxalosazone from formaldehyde 
and accounts for its formation by the aldol condensation of form- 
aldehyde to gtycollic aldehyde. 
Degradation of Sugars. 
[Trans. Chem. Soc. 1900. 1294.] 
The direct and systematic transformation of a higher to a lower 
member of the aldose sugars was first effected by Wohl [Ber. 1893. 
740 et seq.\ The oxim of the sugar is first obtained by the action 
of free hydroxylamine and is then acted upon by acetic anhydride 
in presence of sodium acetate. In this way the nitrile of the 
corresponding acid results and all the hydroxyl groups become 
acetylated. Glucoseoxim for example yields the nitrile of pent- 
acetylgluconic acid, and arabinoseoxim gives the nitrile of tetr- 
acetyl arabonic acid. These products readily lose the elements of 
hydrocyanic acid by the action of silver oxide or of alkalis yielding 
a derivative of the lower sugar. 
This method has now been applied in the case of glycollic 
aldehyde. Alcoholic hydroxylamine gives the corresponding oxim 
in a syrupy and impure condition, but when the product is treated 
with acetic anhydride as in Wohl’s experiments it gives the acetyl 
derivative of glycollic acid nitrile, or acetoxyacetonitrile, 
CH 3 CO . o . ch 2 cn. 
This when treated with ammoniacal silver oxide yields a product 
which when acted upon by dilute sulphuric acid gives formalde- 
hyde. Wohl has since obtained glycollic aldehyde from glyceral- 
dehyde, so that only the degradation of tetrose to triose is 
wanting to complete the entire series from hexose. 
A second systematic method of bringing about the degradation 
of sugars is that based upon the oxidation of the corresponding 
acids by hydrogen dioxide in presence of iron. This was first 
effected in case of tartaric acid, a normal oxidation-product of 
tetrose, in the manner described above; the degradation here 
extends over two stages — tetrose to diose — and an intermediate 
product — dioxymaleic acid — can be isolated. The initial operation 
