— 136 — 



rangement must take place of the camphene-type into the camphor-type; 

 possibly on the lines set forth below: 



CH-CHa 



Camphenylic acid. 



CH 



CH 2 



H„C 



COOH 



C-COOH 



Tricyclene carboxylic acid. 



C(CH. ? )-> 



H 2 C\ /COOH 



C 

 COOH 



Carboxyl apocamphoric acid. 



Lipp is of opinion that these experiments prove the uniformity of 

 camphene from isoborneol. 



On the formation of isobornyl formate from camphene see p. 142. 



^-Pinene. M. O. Forster and S. H. Newman 1 ) have discovered that 

 when an alcoholic solution of pinene nitrosochloride is heated with sodium 

 azide, pinene nitrosoazide is formed. This substance appears in the form of 

 brilliant, colourless, transparent prisms, m. p. 120°. When this compound 

 is treated with acetic anhydride there results the acetyl derivative (m.p.64°); 

 treatment with sodium alcoholate yields nitrosopinene. A modification 

 melting at 126° is obtained by heating the pinene nitrosoazide with water 

 and alcohol. This isomeride also, when treated with sodium alcoholate 

 yields nitrisopinene; its acetyl compound melts at 71°. When the pinene 

 nitrosoazide melting at 126° is heated with water it yields hydroxydihydro- 

 carvoxime, which substance was also obtained from terpineol nitrosoazide, 

 m. p. Ill ° (a body also prepared by the authors) by treating it with sodium 

 alcoholate. The molecular structure of these bodies is shown below: — 



x ) Journ. chem. Soc. 99 (1911), 244. 



