130 REPORT OF SCHIMMEL & Co. APRIL 1914. 
H.C eee H2C ee 
H;C-C-CHs | AsC-C-CHs 
ae eee Hic | cho cae 
p70 : OH ft 
oO G 
C=N-OH CK 5m 
(I) Sulphuric ester of 2-hydroxyapo- (Il) 2-Hydroxyapocamphane 
camphane hydroxamic acid. hydroxamic acid. 
H.C Cee H.C Obes HeC Th ee a 
C-COOH C- COOH C:CH-NOz 
(Ill) 2-Hydroxyapocamphane (IV) Tricyclenic acid. (V) Nitrocamphene. 
carboxylic acid. I 
Pergo vvnyeti tanta! H.C seer 
H;C-C-CHs H3C-C-CHs 
mc nl CHBr H.C ieee 
Cc £N-OH CN 
“Br 
(VI) 2-Bromoapocamphane hydroximic (VII) Nitrile of the apocamphane 
acid bromide. carboxylic acid. 
Bornylene. In continuation of previous investigations’), G. G. Henderson and 
W. Caw?) have oxidised bornylene with hydrogen peroxide in an acetic solution, the 
bornylene having previously been purified by the method described by Henderson and 
Caw*). The most favourable temperature for carrying out the oxidation-method is 
from 55 to 60°, acid and neutral products, with a trace of an aldehyde, being formed. , 
The first-named two bodies consisted of two acids, volatilising with steam: camphenanic _ 
acid (m. p. 95°) and isocamphenanic acid (m. p. 74°), as well as of a non-volatile ; 
hydroxy acid CsHi2(OH)CO:H, which did not crystallise and which decomposed when 
distilled im vacuo, giving rise to an unsaturated acid, melting at 80°. The neutral 
oxidation-products consisted of a mixture of esters, of which those which volatilised 
with steam, when saponified, yielded in addition to acetic acid, the three acids mentioned 
above, as well as two isomeric alcohols CioHizOH. As was to be expected, the 
alcohol-mixture consisted principally of borneol. The second alcohol was identified 
as epiborneol by oxidising it into epicamphor*). The esters which did not volatilise — 
with steam, when saponified, afforded the same acids as well as two isomeric saturated 
alcohols Cio9HisO2, respectively melting at 247 to 248° and at 235 to 236°; these latter — 
were separated out from benzene by fractional crystallisation. So far nothing definite — 
has been ascertained concerning the structure of these alcohols. The alcohol with 
1) Comp. Report October 1911, 134; April 1912, 169; April 1918, 135. — *) Journ. chem. Soc. 108 (1913), 
1543. — %) Comp. Report October 1912, 147. — +*) See p. 140. og 
