CR SP ape DEE REE alr n Tonal cian CALTON % elit: IADR T WBE ee eye 
1: 3 mm). By t heating tie hydrazone as aod and aeanek in a teealed tube, 
Bper ieyclocamphane- (VI) is obtained; m.p 117 to 118°, 'b.p. 150 to 152°. This hydro- 
carbon Bis: even” more volatile than camphane;, on eeee in closed cai vessels it, 
° (16 ea 189° to. “190° ford.” ee) The faiaiecora refraction or ‘Beperteyelo- 
; aphanol ‘methyl éther was 48. 8156, calculated for CHisO<<,48.041. The difference, 
0.77 - points to the presence of a tricyclic ring which, vACCOTEIE: to recent observations, — 
“causes an exaltation of + 0.65 to | 0.85. | 
ae oxime. Since its melting point was indefinite it may probably be the 
e of “stereoisomerides. On treatment with dilute sulphuric acid, the oxime passes — 
es er ‘into cyclocampholenic nitrile (VIII), a viscid, paraffine- -like mass. melting at 78 to 
80°. ‘The ‘saponification of the nitrile to the acid (IX) was effected only with difficulty, 
best. method being heating with a 25 per cent. solution of caustic potash in a sealed 
Bite. to 100° for some time. The acid melts at 108 to 110°. By. heating the silver 
“salt | with ethyl iodide, Bredt and Holz obtained the ethyl ester; b.p. 111 to 112° (14.5mm.).. 
ae dation of eyclocampholenic acid with potassium permanganate or chromic acid mixture 
a 
Sg P. 228 £0. 2309 2 8 es : 
4 the Gradation: of ‘this ketone. Pe was very seable cowards alae boone the only 
inite oxidation product yet obtained being oxalic acid. When camphenilone, however, 
is heated with dilute nitric acid -in a sealed tube to 140 to 150°, there result as 
Ze xidation-products crystals of ‘the m.p. 90. to 92°, an oil, -and isocamphoronic acid; 
- pos ssibly, the crystals and the oil are tertiary nitroketones. ‘The formation of isocamphoronic’ 
2 cid was to be expected on account of the accepted formula for camphenilone.. The 
first oxidation-product is probably an «-nitroketone which is then ayerohesd and 
su bsequently oxidized. ap | hy | 
\! 
ee 
fe ctions of this body are most easily explained thereby. An unobjectionable synthesis 
of this ketone had hitherto not been carried out, although this was neccessary as a 
ity, and well-cheracterized derivatives, such as enone acid from camphor, have 
een obtained from fenchone. te 
a Only. now L. ai has Se in verifying Semmlers's fenchone formula by . 
a At first, nie tried to start ae a methyleyclopentanonic acid, a | product of the splitting 
of P-fencholenic acid; the structure of the latter acid is well-known, since it yields, 
130 Report April 1906, 124, 2 fy} Bericnte 50 91, 1362. 
3 Ae y Evd- Chea war ACnwie te tp toss ae ; : 
al is i ms Wea ees ae Ae aA NOS: wy poy ee ta ¥ He Le 
proof for the correctness of Semmler’s formula, fenchone being cherecterized by great 
SS oxime op 8-pericyclocamphanone was prepared according to the method approved - oS 
A 
yh 
to cycloisocamphoronic acid (X),.a Bony crystallizing in small colourless ‘scales Ob % 
_ Fenchone. = Semmiler’ S*) formula for fenchone iS now generally see pied: since the eo 
