344 
Wisconsin Academy of Sciences , Arts and Letters. 
a molecule of hydrogenchloride (molecular addition); its unsaturated 
condition becomes apparent from the hydrochlor nitrosate. Thus far a 
separation of two nitrosates, if such a mixture results at all, has not 
been effected. 
Nitrolamines. 
The double decomposition of terpinene nitrosite with bases on the part 
of Wallach induced this investigator to study the behavior of nitroso- 
chlorides and nitrosates toward bases. Thereby the analogy between the 
nitrosochlorides 
No 
Cl, nitrosites 
No ( NO 
O (NO) and nitrosates } O (NO a ) was 
established. The application of this reaction proved especially favorable 
in the limonene group. Even before the nitrosochlorides were known 
to be a mixture the notrolanilids were recognized as such. Further¬ 
more, it was ascertained that the separated a and (5 nitrosochlorides 
yielded each two, viz, an a and a (5 nitrolamine base, and that these a and 
/3 nitrolamine were respectively identical. The reactions may be ex¬ 
pressed in the following manner: 
a — Nitrosochloride ft — Nitrosochloride 
a — Nitrolamine fi — Nitroamine 
(NO 
a-Nitrolpiperidine 26 . C 10 H 16 -j 
(n.C 5 H 10 
Limonene-a- nitrol piperidine crystallizes from alcohol in hand¬ 
some rhombic crystals which melt at 93-94°. In petroleum ether, in 
ether and chloroform it is readily soluble, less so in alcohol. The solu¬ 
tions turn the plane of polarized light in the [direction® of the underly¬ 
ing hydrocarbons: [or] = + 67, 75° resp. — 67, 60°. The hydrochlo- 
1 CZZ□ 
rides turn the plane of polarization in the opposite direction. 
The dipentene base precipitates upon the mixture of the petroleum 
ether solutions of the optically active components. From alcohol it 
crystallizes in monosymmetric crystals which stand in no relation to 
the well formed crystals of its optically active modifications. 
(NO 
/?- Nitrolpiperidine 26 C xo H T6 ] 
(n.c 5 h T0 . 
The Limonene derivatives melt at 110-111°, crystallize monosymmet- 
rically, and are less soluble, especially in petroleum ether, than the 
