eee eee Gb a ie! ste . Pas ap ta Oe % HA a sor Waa ‘ey 
“4 > t Ch S He 
Ss SN 
: > solid iteosbchlorides: Weyl ' states. that solid Bie ssocilntides are formed principally 
as the grouping RC: CHR. Tsofenchylene is likewise an exception from these rules. 
: pact be distilled without decomposition. The isofenchylene from the xanthate boiled from 
138.5 to 141° and manifested the properties ‘described by Kondakov and Lutchinine?).- 
. ‘On oxidation. with KMn0Osg i is yielded cs-l-rsofenchoic acid, m.p. 157 to 157.5°; with bromine 
and with hydrogen chloride, only oily products were ‘obtained, whereas the nitrosochloride 
_and the nitrosate were solid bodies; the former melfed at 1429, the latter unsharply. 
3 One ‘comparing the cyclofenchene prepared by Qvist with an original preparation 
3 of Micron sy: of S-pinolene from pinene hydrochloride the former proved to be a feebly. 
_ dextrorotatory d-cyclofenchene, the latter a mixture of /- and d, /- -cyclofenchene. Aschan’s 
_ hydrocarbon, namely, yielded on bromination two solid dibromides, of which one was 
_ preparation actually showed a distinct, although very weak Izevorotation:. —- [@}piso — 028°. 
___ Finally, Qvist studied the behaviour of the solid dibromide (m. p. 87 to 88°) resulting - 
* from cyclofenchene as well as from a-fenchene. On treatment with zinc and alcohol, 
d. a-fenchene dibromide yielded 1, a-fenchene and fenchane. This result, however, allowed 
on not of BIaW RIE any positive conclusions as to the constitution of afenchene dibromide. 
oR. H. Roschier*), ina lengthy paper, reports on the ozonisation if apebommylent Le 
_ and Hintikka®) on the same subject. It was now proved that the hydrocarbon hitherto 
- termed apobornylene is a mixture of two isomeric hydrocarbons, of which one is real 
apobornylene (I), the other being tricyclic apocyclene (Il). Furthermore, Roschier found 
the formula proposed for, d- -fenchene*) — identical with Wallach’s D, /-fenchene — was 
fully confirmed. The second semicyclic, -6-fenchene, being identical with. Wallach’s 
D,d-fenchene, is constituted as per formula IV.- The hydrocarbon of the b. p. 145 to 
ure has, in its main part, the double linking in the cycle, as is showed by formula V. 
“The lowest-boiling fenchene possesses for certain the formula VI suggested by Semmler 
for isoallofenchene. In the low- boiling fractions of fenchene, a small amount ‘of cyclo- 
_fenchene, identical with Aschan’s. 8-pinolene, is found. 
The apobornylene used in Roschier’s experiments was prepared in one case from 
_camphenilol by means of Tchugaeff’s xanthate method, in another case from camphenilone 
_and its dichloride. The hydrocarbon obtained from camphenilol methyl xanthate was 
a tough, camphoraceous body, m. p. 38°, b. p. 138° (760 mm.).. The product from 
cooling. On dry distillation of camphenilylamine phosphate, in a CO,-current, according 
to Harries, there was formed camphenilylamine, and not the hydrocarbon expected. 
When ozonised, apobornylene yielded a solid ozonide ColHisO; of normal com- 
- position which was fairly stable at ordinary temperature and which was split up, in 
_ glacial acetic acid solution, chiefly into three fractions of which the one of the lowest 
boiling point was an oil with an ester-like smell. The medium fraction had aldehydic 
et 
1) Die Methoden der organischen Chemie. Leipzig 1911, vol. Il, p. 639. — _*) Chem. Ztg. 25 (1901), 131; 
Journ. f. prakt. Chem. \. 75 (1907), 540; Reports April 1901, 64; October 1907, 148. — 4) Liebiy’s Annalen 387 
(1912), 49; Report April 1912, 188. — *) Annal. Acad. Scient. Fenn., Ser. A. 10 (1919), No 1, p.1; Chem. Zentralbl. 
1919, 1. 726. — 5) Liebiy’s Annalen 387 (1912), 296; Berl. Berichte 47 (1914), 512; ‘Reports April 1912, 187; 
ebei 1915, 95; October 1918, 117. — %) Misprint, in lieu of -ce-fenchene ? : 
‘ -- 4 ‘ - 
_ Qvist obtained this. hydrocarbon from isofenchyl xanthate which even im vacuo could — 
_ identical with /, «-fenchene dibromide, the other with d,l-fenchene dibromide. Aschan’s © 
3 of the various fenchenes. This work isa continuation of the investigations of Komppa ~ 
the fenchene hydrocarbon to consist of a mixture of at least five terpenes, two of 
- which are semicyclic, two endocyclic, and one tricyclic. As was proved by ozonisation, ) 
_camphenilone remained oily at ordinary temperature and congealed only after slight 
ar 
