— 176 — 



reached by analogy that both «- and /?-pinene produce an equal yield of 

 solid, and consequently also of liquid, hydrochloride. On the other hand, 

 it is also possible to calculate in advance, from a mixture of «- and 

 /?-pinene and their optical antipodes of known percentage, the index 

 of rotation of the hydrochlorides which can be prepared from them. 

 A comparative table of the values found and calculated for the individual 

 oils appears to confirm the accuracy of this theory, but Vavon is mistaken 

 in looking upon his results as confirming the observations of Semmler, 

 or those of Ahlstrom and Aschan 1 ). The two last-named, in con- 

 tradistinction to Vavon, did not invariably obtain equal yields of hydro- 

 chloride from the individual fractions of their American and German oils. 

 From the high-boiling fractions they obtained much smaller yields of hydro- 

 chloride than from those of lower b. p., and the latter, also, did not 

 consist exclusively of pinene. On the contrary, Ahlstrom and Aschan 

 lay stress upon the fact that for this reason they abandoned their original 

 assumption that only Semmler's "pseudo"(,#-)pinene was to be considered 

 as the second source for pinene hydrochloride from the higher fractions. 

 In the high-boiling fractions of turpentine oil, they surmise the presence 

 of limonene, camphene, and possibly, although not probably, of cymene. 



In one of our last Reports 2 ) we mentioned that Barbier and Grignard 

 had hydrated French oil of turpentine with a view of obtaining a knowledge 

 of the various constituents of the oil. With the same object in view 3 ) 

 they have examined liquid pinene hydrochloride prepared according to 

 Barbier's method 4 ) from French oil of turpentine. This body, which is well- 

 known to consist of a mixture of solid hydrochloride of pinene with iso- 

 merides which, so far, have been scarcely investigated, was converted 

 into its magnesium compound and the latter exposed to the action of 

 oxygen and carbon dioxide. By this method the investigators succeeded 

 in demonstrating the presence, in the liquid hydrochloride, of bornyl chloride 

 and a small proportion of fenchyl chloride, but not of true pinyl chloride 

 (pinocamphyl chloride according to Wallach), the occurrence of which in 

 the liquid hydrochloride had been suspected by the authors. 



The new body C11H19NO2, m. p. 101 to 102°, which was obtained by 

 Deussen and Philipp 5 ) in the process of splitting off hydrochloric acid 

 from pinene nitrosochloride by means of sodium methylate has lately been 

 more closely investigated by the authors 6 ). Pinene nitrosochloride pre- 



x ) Comp. Report October 1906, 75. 



2 ) Report October 1909, 167. 



;i ) Bull. Soc. chim. IV. 7 (1910), 342. 



4 ) Ibidem 1883, 323. 



5 ) Liebigs Annalen 369 (1909) 62; Report April 1909, 168. 

 «) Liebigs Annalen 374 (1910), 112. 



