122 



with camphenilone or fenchone. Semmler gives the following for- 

 muloe for the separate processes: — 



H 3 C >c/ 



HX=C 



CH 



X CH 

 CH 



\ 



H 3 C \ 



CH 

 '\ 



X CH 2 



CH 2 



CH 



CH 



/ 

 CH 



Camphene 



CH 



\ 



H 8 C 



Scf 



/ 



CH 



OC 



X CH 2 



CH. 



H 3 C 



HX/ 



/ 



/ 



HX 



^ 



H 3 C 

 HOO( 



C 



I N CH 

 CH 



CH 2 CH 



Ozonide 



I 



CH 



\ 



\ 



H C' I 

 - 8 ^ OH CH, 



X CH 2 H3 ° X C/ 



-> n ^ O CH 



/ 

 CH 



CH 9 HOOC 



N I / 



\l/ 

 CH 



Camphenilone 

 CH 

 X CH 



CH H„C HC 



CH 



CH, 



CH 





o a 



/ 

 CH 



Isocaraphene ozonide 



1 



CH 



\ 



x I / 

 V 

 CH 



CH Q 



o=cl 



\ 



H 3 C \ / 



3 x c/ 



HX / 



CH 



CH„ HX-HC 



x CHO 



CH 2 



/ 

 / 

 CH 



CHO 



Unsat. acid 



C 9 H 14 2 



<5-Hydroxycamphenilonic Lactone Dialdehyde 



acid m. p. 95 to 96 



Terpinene. F. W. Semmler 1 ) has made a critical study of the 

 statements recorded relating to terpinene obtained by various different 

 methods. He calls attention to the fact that there is a series of 

 contradictory statements on this subject, especially as regards the 

 exaltation which has been observed, and the formation of the nitrosite. 

 His experiments, which are described below, point the way towards a 

 clearing-up of this involved condition of things, but the results obtained 

 do not even now permit of any certain conclusions to be drawn. By 

 treating carvenone with pentachloride of phosphorus, without application 

 of heat, Semmler obtained a monochloride of carvenene, C 10 H 15 CI, 

 which was converted into carvenene, C 10 H 16 , by reducing it with 

 sodium and alcohol. This body possessed the following constants: 

 b. p. 179,5 to 180,5° at 735 mm. press., 61 to 63 at 10 mm. press., 

 d2o° 0,844, n D i?49Ij molec. refraction, found 46,74, calculated for 

 C 10 H 16 /2~ 45,24. According to its origin, this hydrocarbon should be 

 Zl 1 ' 3 -dihydrocymene, and might therefore be identical with terpinene 2 ). 

 But, in contradistinction to the observations which have been made 

 on terpinene, carvenene showed an exaltation of about 1,5, On the 

 other hand it gave the nitrosite reaction, although not very readily. 

 This experiment shows that conjugated cyclic linkings may cause exaltation. 



Up to the present no inversion had been observed in the treatment 

 of terpinene with acids. But when carvenene was boiled for two 



*) Berl. Berichte 41 (1908), 4474; 42 (1909), 522. 

 2 ) Compare Report November 1908, 175. 



