The Limonene Group of Ter penes. 
347 
The limonene derivatives crystallize from alcohol in beautiful, hexagonal 
tablets and melt at 78° . They are not at all strongly optically active, 
but turn the plane in a direction corresponding to that of the underly¬ 
ing hydrocarbons, [or] = + 12.91° resp. — 12.51° . The hydrochlor ad¬ 
dition product of Dipentene-(3-nitrol-anilid crystallizes from its alcoholic 
solution in four sided prisms and melts at 90° . 
Hydrochlor, Nitrosochlorides, Nitrosates and Nitrolamines. 
Through the action of hydrochloric acid, amyl nitrite and nitric acid 
( NO Cl 
upon “carvene” Maissen obtained a “compound C 10 H 16 j jj ’’which 
Wallach recognized as hydrochlornitrosate, C 10 H 17 Cl. NO (O. NO s ). 
Later it was shown that this compound was a dipentene and not a lim¬ 
onene (“carvene”) derivative. The corresponding hydrochlor-nitroso- 
chloride was first prepared by Wallach. The optically active modifica¬ 
tions were prepared by me in Prof. Wallach’s laboratory. 
The hydrochlor-nitrosochlorides, etc., are saturated compounds. They 
can be regarded as nitrosochlorides, nitrosates and nitrolamines of the 
monhydrochlorides of the limonene hydrocarbons. Thus far all of the 
saturated nitrosochlorides, etc., prepared from monhydrochlor limonene, 
have been obtained in but one modification, which corresponds to the 
u-modification of the unsaturated derivatives free from chlorine. 
( NO 
Hydrochlor nitrosochlorides 31 C- 10 H 17 Cl ] 
(Cl 
The limonene derivatives crystallize poorly, melt at 92-93° without de¬ 
composition. [a] for the dextrogyrate compound = +173.71°. The crude 
product is largely contaminated by the dipentene modification. The 
latter apparently posseses a higher melting point, viz, 109°. Like the 
unsaturated nitrosochlorides they split off hydrochloric acid, however, 
to form hydrochlorcarvoximes. 
( NO 
Hydrochlor-nitrosates 32 C 10 H 17 Cl-j 
( O (NO,) 
The limonene derivatives can be obtained in handsome pearly prisms. 
They melt at 108° decomposing at the same time, [or] for the dextro¬ 
gyrate compound = +61.34°. The dipentene hydrochlor-nitosrate also 
melts at 108-109° and is readily distinguished by its optical activity. 
From it a molecule of nitric acid can be split of with the aid of dimethyl- 
anilin 33 anologous to the hydrochlor carvoxime reaction. The resulting 
