ne 1t=1729), ‘he Rplaced this along with excess a ae in the pressure tube, 
an ‘converted it to the monohydrazone (VII), and finally obtained, as per Kishner 
iy (heating with sodium ethylate to 180 -195° under strong pressure), the. ee 
tricyclene (m. p. 64— 65°), almost quantitatively by the Splitting-up of the hydrazone. eo 
The hydrocarbon was only stable for a short time in cooled glacial acetic solution * 
== ate 
in the presence of permanganate; on gentle heating it yielded tricyclenic.acid anda  — 
carbonyl compound as oxidation products. This showed that the splitting-up of the) pe 
-hydrazone had taken place normally, and that er. and tricyclenic acid nave the eye 
same ring system. | | | 
a Of interest also was the fact that tewelatte: under the same experimental Con 
ditions as borneol (digesting with sodium bisulphate at. 1609), but not like isoborneol — 
(digesting - in benzene solution with zinc chloride), yielded the final product camphene. 
“Hence tricyclene can be regarded as an intermediate product in the formation of 
_camphor from borneol; not however as intermediate product in the splitting off of Pe 
“water from isoborneol. Thus the Wagner rearrangement, as Ruzicka’) seems to 
assume, cannot be schematised by introducing a tricyclene —the symmetrical tricyclene ie i. 
Aa wit—as an. intermediate stage in the manner of formation. of ordinary camphene. Pia 
: ee According to Meerwein: *), the addition phenomena i in the interchangeable transition oe 
of isoborneol to ‘camphene is to be traced to the existence of a tautomerism between y . 
the esters ay isoborneol and camphene hydrate. — ! 
Riven + 
eas? FC eh De ELC C—O 
eee Eee ee Cs CCH, a = CH, C-CHs i 3 
a hes ote St sei ees, {Sp COOH {Pips coal lee : C. CH, : ; S 
Groat,’ : mt a, @ THeaefenie acid. (Il) Tricyclene. . 
isa Ne ot ch Pk CEG Sas CH; 
Laem a ee | fy ai at ae i CH;-C- CH L, 
Bes 25 PCH. ‘NH, rare ee “HC. ce 
cs Sea pae @-Aminotrieyclene. His 
sie ae je pan cae IY) Camphenilane aldehyde. 
7 ay Y ' 
ee Cotas CH0H — Gib: cé \H BORG Rong oe CH: N-N: CH: Colts Son 
4 bg AW Trieyctol. . ma) Tricyclal. . eet Vd) Treytal Waa aie. 
& eo fe Sh _CyH,3-CH :N-NH, —> ichlin 
A * et . OI Tricyclalmonohydrazone. ' Tricyclene. 
Be oe Helvetica chimica acta 1 (1918), 124, 130; Report 1919, 115. — *) Zeitsohr. f. angere. Chem. 88 (1920), IL. 365. 
