— 99 — 



The oxamino-oxime crystallises out in stout crystals and melts at 

 164 to 165°. It is readily obtainable with an excess of hydroxylamine, 

 and on account of its low volatility it can be separated without difficulty 

 from the ketone and the oxime. 



0,1586 g. subst: 0,3476 g. C0 2 , 0,1461 g. H 2 0. 

 Found Calc. for C10H20N2O2 



C 59,78% 59,96 °/o 



H 10,24% 10,07%. 



That this additive product of hydroxylamine possesses the con- 

 stitution of an oxamino-oxime, of which the structure is similar to that 

 of carvenone oxamino-oxime, is shown by the similar behaviour of the 

 compounds 1 ). When heated, the oxamino-oxime immediately decomposes 

 Fehling's solution; when alcoholic solution of the oxamino-oxime is boiled 

 with mercuric oxide the mixture at once assumes a blue colour 2 ). These 

 two tests show that the menthenone hydroxylamine derivative contains 

 a NHOH- group, which under oxidation with mercuric oxide is trans- 

 formed into a nitroso-compound identifiable by its deep blue colour. Hence 

 menthenone oxamino-oxime must possess the corresponding formula: — 

 CH 3 CH 3 CH 3 



c 



/\ 



H 2 C CH 







C — NHOH 

 /\ 

 H2 C CH2 



C — NO 

 /\ 

 H2 C CH 2 



^ I 



H 2 C C = 



\/ 



CH 



H 2 C C=NOH 



X/ 

 CH 



H 2 C C=NOH 

 CH 



CH CH CH 



/\ /\ /\ 



H3C CH3 H3C CH3 H3C CH3 



Attempts to attach hydrochloric acid, hydrobromic acid, or bromine 

 to the ketone, were unsuccessful. At a low temperature, for instance, 

 the ketone absorbed the quantity of bromine calculated for one ethylenic 

 bond, but at ordinary temperature hydrobromic acid was rapidly given off. 



Mention may be made, in conclusion, of the following experiments 

 made by us, from which it is evident that the new peppermint ketone 

 really possesses the structure of a zl^menthenone-S. 



Elimination of water under formation of p-cymene: When 

 phosphoric anhydride 3 ) or benzoyl chloride 4 ) is allowed to act upon 

 carvenone, p-cymene is formed. This hydrocarbon can also be obtained 



*) Harries, Berl. Berichte 31 (1899), 2896. 



2 ) Piloty and Ruff, ibidem 221 ; Harries and Jablonsky, ibidem 1379. 



3 ) Bredt, Liebig's Annalen 314 (1901), 381; Report April 1901, 68. 



4 ) Marsh and Hartridge, Journ. chem. Soc 73 (1898), 856. 



7* 



