— 137 — 



which he calls pinolene (d~ 0,8599; Wd + l ^5°l n D M5768; 

 mol. refr. found 43,2, calculated for C 10 H 16 / — 43,53). The molecular 

 refraction shows that it is a bicyclic hydrocarbon with one double bond. 

 By introducing hydrogen chloride into the ethereal solution of the 

 terpene in the cold, a chloride C 10 H 17 C1 (m. p. 38 ; [a] D -(- 9,78°) 

 was formed, which had a menthol- and camphor-like odour, and 

 which readily splits off hydrochloric acid already when left standing 

 in a closed vessel, or when brought in contact with water. 



In chloroform solution pinolene absorbs one molecule bromine, 

 but it does not yield a nitrosochloride, nor a nitrosite or nitrosate. 

 It does not change when boiled with 20 per cent, oxalic acid solution 

 or 10 per cent, sulphuric acid. By potassium permanganate solution 

 it is attacked with somewhat greater difficulty than pinene, and there 

 is then formed, besides other products, a syrupy acid which crystallises 

 after some time (m. p. about 200 ). Treatment of pinolene with 

 glacial acetic and sulphuric acids according to Bertram and Walbaum, 

 led to the acetate of an alcohol C 10 H 17 OH (b. p. 202 to 203 ), which 

 was oxidised to the ketone C 10 H 16 O (b. p. about 200 ). The 

 semicarbazone of this ketone does not appear to be uniform, as it 

 showed various melting points (about 220 and 224 to 225 ) accord- 

 ing to the crude material employed, and the mother liquors contained 

 another crystallising semicarbazone. 



When equal quantities of pinolene hydrochloride and aniline were 

 brought together, heat was spontaneously evolved, and aniline hydro- 

 chloride separated off. After working up the product, a hydrocarbon 

 was obtained (b. p. 154 to 155 at 750 mm. pressure; d^o 0,8648; 



Wd + 5>46 , n D20,8° i>47°55; mo1 - r efr. found 43,77 , calculated 

 for C 10 H 16 / — 43,53), which is neither identical with camphene nor with 

 pinene, but which the author, on account of its resemblance to the 

 latter, calls is opine ne. It is also a bicyclic hydrocarbon with one double 

 bond, and absorbs one molecule bromine and one molecule hydro- 

 chloric acid. The chloride C 10 H 17 C1 (m. p. 36 to37°; Md22° -|-9,i8 ) 

 is as unstable as that of pinolene, and is also decomposed by aniline 

 already in the cold, when it again yields back isopinene. Aschan 

 reserves for the future a final decision on the identity of the two 

 chlorides which would follow from this. Isopinene also yielded neither 

 a nitrosochloride, nor a nitrosite. On treatment with glacial acetic 

 and sulphuric acids according to Bertram and Walbaum, there is 

 also formed an alcohol (b. p. 202 to 203 ) wich can be oxidised into 

 a ketone (b. p. about 200 , m. p. of the semicarbazone 22 1°) with a 

 menthol-like odour. When boiled with dilute sulphuric acid, isopinene 

 is not split up, as well as pinolene. The author holds out a prospect 

 of further information on the subject. 



