hye Pecarbon: “obtaened ero Aeaehor as well as froth Pachore boiled at 172 to 
175°; m. p.71 to 73°. On hydration by means of glacial acetic and sulphuric acids, 
bc both hydrocarbons yielded the identical acetates which on saponification gave the same 
alc sohols. and, on subsequent. oxidation, the identical ketones and dicarboxylic acids. | 
As to the constitution of the ‘hydrocarbon, the oxidation with. potassium permanganate — 
oftere a clue, since it revealed that the hydrocarbon was very stable towards that — 
ag Evidently, the hydrocarbon has the constitution of a “homocyclene”. This 
formula explains best the fact that, on hydration by means of glacial acetic and 
sulphuric acids, an acetate CisHo2O. is obtained with the boiling point of iso-borneol; 
the acetate giving on saponification a secondary alcohol C1iH900, m. p. 193° (phenyl- 
u rethane, m. p. 102°) which in turn gave, on oxidation, a a ketone CuFtisO (m. p. 167 to © 
168°; oxime, m. p. 125 to 127°) yielding an acid CitHeOx; 'm. p: 191° (anhydride, ; 
m. p. 205 to 207°). All of these products might be derivatives either ‘of camphor c or 
ae idea Chie Ce ~ [eC 
As C(CHa)2 6H -} if GHs On 
3 | i" 5 
‘ H Cc! ct te beer r H.C. ‘ull Gee diag 
os ~ ree emt ; ; ape cH SNe ees Oe 
ee "as ee eC (eae Ave mama hua en ae! | 
s panes eae) Methylborneol. . (et pL els ome ree ee oF 
ear 2 ate Be CH ata PRO RUC RRR ERR oo 
ea a HC ae yt tees } a 
C(CHy)2 | pee 
ste a tana ee CH, Ba ety : 
BF Pe GO Sy Hate el ae 
(ILD). Homocyclene. ae. eee AC NOR UNE er 
of the paeydedus acid, etc., however, point to. their relation to the camphor series, . 
- hich was furthermore pean by the measurement of the molecular refraction of the 
diethyl ester of the acid C1i1HisOx. In this degradation, the hydrocarbon Chr. behaved 
Ci:H,.0 is termed by Bredt sec. 8-methylcamphor. | ee Gane 
: % When camphor is submitted to Grignard’s reaction with phenylmagnesium bromide, 
phenylborneol results, which was obtained already by A. Haller and E. Bauer*), and | 
which may be separated from unattacked camphor owing to its low volatility. On 
eine phenylborneol with acetic anhydride, a liquid hydrocarbon CrsHoo is the result; 
acids, an acetate is formed (m. p. 87°; b. p. 136° at 2 mm.), in addition to a hydro- 
carbon apparently isomeric with the original one; d° 1.0034; [<]p — 3.759; b. p. 86° 
(2 mm.). The hydrocarbon yielding the acetate ees not add hydrogen chloride; the 
one boiling at 86° (2 mm.) forms a hydrochloride, m. p. 76.5°, from which on treatment 
vith milk of lime a tertiary alcohol, isomeric with Bieabomed! is Pact b. p. 
106.5° (2 mm. pes [lore U2) rie Za i 
¥ E 4) Cabvive, for BIR, ae Report October 1905, 100. — *) Compt. rend. 142 (1906), ‘77; Report October 1906, 120. 
Be: 3 
pa 7 
ne 
{ f (ee 
° isofenchone; many of their properties, e. Js; “smell, Creatine form, easy formation “8 +7 
like its lower homologue, cyclene which, on hydration with glacial acetic acid and ~ 
sl Iphuric acid, yields quantitatively isobornylacetate’. The diethylester of the acid i 
CuHis0, shows d73 1.0289; the new acid is a 2-methylcamphoric acid; the ketone 
5 0.9920; [@]p + 3.279. When brought in reaction with glacial acetic and sulphuric 
