AOR acs PRepoRe | OF : SENOS % Co. “APRIL O ( 
obtaining caronic acid, trans-caronic acid was finally “obtained “Tile 
‘no doubt that the constitution of carene corresponds to one of the two. for 
The normal molecular refraction of the terpene points to the absence of 
position of the double\hond to the three-ring, and hence speaks for formula a 
is the only terpene found in nature up to now with a carane-ring. . 
From the 149 to 155° (36 mm.) fraction of the original oil, the sesquiterpene 
rather viscid oil with a weak, not oe smell, and the followin constants 
b. p. 254 to 256° (706 mm.), 150 to 151° (36 mm.), qm? 0.9284, [2]p + 42.739, mp0! 40 
mol.-refr. 64.15. The molecular refraction leads to the conclusion of the tricyclic 1 nati 
of the compound. With the halogen acids d-longifolene yielded beautiful crystal 
derivatives; the melting point of the hydrochloride lay between 59 to 60°, that of 
Eoagabeantioe between 69 to 70°, and the hydriodide melted at about 71°, 
CH— CH —CCI1:(CHs). CH.— CH 
cH. cS Yen i He ek Son-oc CCl: Hc 
‘CH,— CHg Noe CH, 
(I) Sylvestrene hydrochloride. (Il) Dipentene hydrechionies ms a 
C-(CH,). Wi a 
CH,-—CH CH+— me 
CHK be oe eR a 
NcH- cH, . ues CH.” Ree ge ne ‘(e 3 
(Ill) 4,7,7-Trimethyl-bicyclo-[0,1, 4]-42-heptene. (IV) bir nantnilot aka |e 
Probable formula of carene (4%-carene). ; . 
oe | eee \ 
CH,— CHK HO CHz CH cana 
CH= << pen De eH 
CH.— CH;; CH; CH(OH)—CHp : ees 
(V) 4-Methylene-7,7,-dimethyl-bicyclo- (VI) 4,7,7- -Trimethyl-3, 4-dihydroxy-bicyclo-[0,1 , 4]-heptane. wh 
[0,1,4]-448)-heptene, dehydrocarane. 
va (CHs)o 
HO CH(OH)— CH 
SOs 
8 | 
ce a ae 
(VH) 4,7,7-Trimethyl-4, 5-dihydroxy-bicyclo-[0,1, 4]-heptane. ‘eee ‘ ON 
| Tricyclene.—P. Lipp+) reports on attempts to obtain tricyclene (Il) itself, by starting — 
with tricyclenic acid. It was first intended to convert the -aminotricyclene (II), which — 
is easily obtained from the nitrile of tricyclenic.acid, into the corresponding alcohol — 
by means of nitric acid. But instead of tricyclol, an oily complex product appeared — 
which had been formed by the rearrangement of the ring system. This easily eae 
aldehyde (IV), and ammonia. ; 
A second series of attempts, starting with the methyl ester of tricyclenic ac 
more successful. The ester could be reduced to tricyclol (V) (m. p. 111-14 
1) Berl. Berichte 58 (1920), 769. 
