— Ill — 



A control of the nitroterebentene, C 10 H 15 N0 2 , previously obtained 

 by Pesci and Bettelli 1 ) by the action of nitrous acid on pinene 

 and subsequent treatment with ammonia, and of its reduction-product 

 amidoterebentene, C 10 H 15 NH 2 , (b. p. 95 [12 mm. pressure]; d 0,9325; 

 n Di9° l A9^°)i ted to the conclusion that in amidoterebentene the 

 amido-group is situated in the side-chain, analogous to the conditions 

 ascertained in /?-phellandrene 2 ). Further, it may be assumed that the 

 base is derived from a methene terpene and that nopinene must be 

 regarded as the fundamental hydrocarbon. The alcohol obtained 

 from amidoterebentene oxalate by conversion with sodium nitrite yields 

 on oxidation with chromic acid first of all a substance with an odour 

 like cuminic aldehyde, whose semicarbazone melts at 20 1 to 203 , 

 and then an acid (m. p. 11 5 ) which beyond doubt represents cuminic 

 acid. For this reason amidoterebentene should contain the picean- 

 ring with only one ethylene -linking, the ring splitting up into the 

 hydrocumin (or cumin) ring: — 



CH 2 CH 2 N0 2 CH 2 N0 2 CH 2 NH 2 



II l/NO I I 



c c c c 



H rt C 



/ 



\ 



CH 



/ 



\ 

 \ 





/ 



\ 



\ 





/ 



\ 



\ 



J-J-g v^ 



CH 3 / 



C 



/ 



-> 



1/ 



C 



/ 



■*-*• 



c 



/ 



-> 



1/ 



c 

 / 



H 2 C 



CH 3 



\ 



/ 



CH 2 



\ 



\ 



/ 





\ 



\ 



/ 



/ 





\ 



/ 



CH 



nopinene 



nitrite 



nitro compound amidoterebentene 



COOH 



I 



c 



CH 



CH(CH 3 ) 2 

 alcohol 



CH(CH 8 ) 3 



cuminic acid 



In continuation of his experiments to convert two isomeric terpene 

 haloid hydrates to some extent quantitatively into a magnesium com- 



x ) Gazz. chim. ital. 16 (1886), 337. 



2 ) Liebig's Analen 340 (1905), 1; Report October 1905, 97. 



