ON NON-AROMATIC DIAZONIUM SALTS. 249 
unlike the decomposable acid diazonium salts of the aromatic series. Double 
salts with auric chloride and platinic chloride have been prepared and are stable up 
to 120° C. in the dry state.” 
CH,N—_C-CH, CH, N__C-CH, 
g Sox | 15, el ana Neon, 
C,H,-N——6o ‘ . C,H,N——co 
VI VII 
Diazoamino derivatives are formed with fatty amines such as dimethylamine and 
are stable up to 120° C., when they begin to decompose into the amine and a complex 
pyrazolone derivative, the constitution of which has not been settled.‘ In this 
series, as in the pyrazoles, the diazonium complex has been replaced by iodine *® and 
by the triazo group® VII, but reduction with stannous chloride does not lead to a 
readily isolated hydrazine, probably owing to condensation taking place with the 
carbonyl group in the ring.” 
‘ Knorr & Geuther, A. 1896, 293, 55; Knorr & Stolz, A. 1896, 298, 58; 
Michaelis, A. 1906, 350, 288. ? Morgan & Reilly, 7. 1913, 103, 808, 1494. 
* Hirsch, B. 1897, 30, 1148; Hantzsch, ibid. 1153. 4 Stolz, B. 1908, 41, 3849. 
5 Michaelis, loc. cit. ° Forster & Muller, 7. 1909, 95, 2072. 
Iso-oxazole Series. 
4-Amino-35-dimethyliso-oxazole has recently been prepared and diazotised. The 
diazonium chloride VIII is very soluble and is much less stable than the correspond- 
ing pyrazole compound. The diazonium aurichloride is sparingly soluble and stable 
on keeping in the dry state at the ordinary temperature.! 
oe *.CMe OMe O0——C-Me 
oye oppo’ tah 120. oR nega LARS SO ie | Non, 
| Yi \ Ss va 
N-—C'Me N——C-Me N——C'Me 
X VI IX 
ys \ 
we BS 
kK DSK 
O—_C-Me sear CMe 0 
Sot | No-w:w-nioZ 
N—C-Me N—C'Me C-Me——N 
XI XI 
The diazonium complex is readily replaced by the triazo group IX and by 
iodine XI. The diazonium chloride reacts, with the base forming a well-defined 
colourless diazoamine XII, and is reduced by stannous chloride to the hydrochloride 
of the hydrazine X. 
‘Morgan & Burgess, 7, 1921, 119, 697. 
Glyoxaline Series. 
The bases of this group have not been studied exhaustively as regards diazotis- 
ability, but 2-aminoglyoxaline when treated successively with nitrous acid and 
alkaline 8-naphthol gave a brownish-red, soluble azo derivative, which does not appear 
to have been isolated.! 
1 Pyman & Fargher, T. 1919, 115, 247. 
1921 © 
