ON SCIENTIFIC RESEARCH. Nek Wii im esa 420 
be purified, and a saturated monocarboxylic acid which was already isolated by Komppa 
and Hintikka, but which was not further investigated by them. Roschier terms this 
acid «-fenchylanic acid; the only structure possible is that of dimethyl-7, 7-bicyc/o-(1, 2, 2)- 
heptane-2-carboxylic acid; m. p. 71.5 to 72°; anilide, m. p.149.5 to 150°. 
_ The mixture of hydrocarbons used for the investigation of 6-fenchene and its 
a companying hydrocarbons was prepared by distilling d,/-fenchyl alcohol (m. p. 33 
to 35°; b. p. 198°), in a current of CO;, with potassium or sodium hydrogen sulphate. 
3-Fenchene is contained in the highest-boiling of the mixture (b. p. 151 to 153°). 
Pr enchene ozonide is a viscous, syrupy oil containing likewise more oxygen than 
th e normal ozonide. By scission, an impure 8-fenchocamphorone was obtained; further 
oxidation gave some apocamphoric anhydride (from «-fenchocamphorone present) and 
in the main an acid obtained formerly by Komppa and Roschier by direct oxidation 
of 3-fenchene. The acid was isomeric with apocamphoric acid and was dimethyl-4, 4- 
cyclopentane-1, 3- -dicarboxylic acid (Nametkin’ s and Chuchrikowa’s*) apofenchocamphoric — 
a cid), m. p. 144 to 145°. Inasmuch as an anhydride was unobtainable, the acid seems 
to be the trans-isomeride. 
| _ The medium fraction of the hydrocarbon mixture, on ozonisation, proved to contain 
an endocyclic double-bond; it represents a mixture of two hydrocarbons, one of which 
is doubtless identical with isoa//ofenchene (VI), the other being probably of the formula(V). — 
Cleavage of the ozonide gave rise, in the main, to a dialdehyde and a ketonic acid. 
The dialdehyde C.H:,O. resulting from isoallofenchene, is a light yellow oil; b. p. 118 
to 120° (10 mm.); d*> 1.0215; Np»0 1.4700; disemicarbazone, m. p. 219°. The crude 
aldehyde fraction contained a small amount of d,/-isofenchocamphoric acid. The 
ketonic acid CioHi,O; is, in all probability, a derivative of the hydrocarbon (V); 
dc © 1.0924: mpuxo 1.4774; semicarbazone, m. p. 220 to 221°. The acid contained the 
g rouping e0: CHs, since on treatment with alkaline hyprobromite solution a 
dicarboxylic acid C,H4,0, (m. p. 147 to 148°) was formed, with splitting-off of bromo- 
form. This acid was not identical with the apofenchocamphoric acid obtained on 
oxidation of §-fenchocamphorone. Probably, it is here a case of the cis-isomeride 
of apofenchocamphoric acid. 
From the degradation-products of the lowest-boiling fraction of the @tenchens 
hydrocarbon mixture there was obtained, in addition to aldehydic and acid compounds, 
a small amount of a volatile, pleasantly smelling, oily ketone C,H,,O (semicarbazone, 
m. p. 209°) which on oxidation yielded a dibasic acid Cy)Hy,O1. The acid fraction, 
contained, besides small amounts of the ketonic acid described above (semicarbazone, 
1. p. 220 to 221°), a fair amount of racemic cis-isofenchocamphoric acid (m. p. 173to 174°) 
and an aldehydic acid which on further oxidation passed over into the same cis-iso- 
fenchocamphoric acid, thus proving that the lowest-boiling fraction oF the fenchene 
hydrocarbons consisted principally of isoallofenchene (VI). 
_ The part of this fraction remaining unattacked on treatment with ozone is a cyclo- 
enchene and identical with Aschan’s -pinolene (VII); b. p. 142 to 143°; dS3- 0.8624; 
Apisso 1.45364; Padrochloride,t m. p. 26 to 28°; hydrobromide, m. p. -+- 4°, b. p. 92 to93° 
2mm.). Cyclofenchene was, “like 6-pinolene, transformed into the acetate of isofenchyl- 
Sicohol, Ae the free alcohol, UE seat and d, -actenchoeainpharic acid. 
Some time Bees A. C. ale 2) eis a new hydrocarbon ‘ fea Seno? occurring 
in the fatty oil obtained from the liver of certain PPA (fishes of the shark ott 
1) Comp. HAS Otober EMI, Ho Ossie: 1918, 133. — 2) Journ. chem. Soc. 111 (1917), 56; 113 (1918), 458. 
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