with M. K Bar swan M. Pp 
eactions of the hydrocarbons camphane, camphenilane and isocamphane. All 
ree contain the identical bicyclic system and differ only by the numbers and 
positions of the methyl groups. They are nitrated by dilute nitric acid (d 1.075) only 
at about 140°, in which behaviour they show analogy with the more constant hydro- 
carbons of the paraffin series. In the main, secondary nitro-compounds are formed; 
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__ The camphane they used, however, was not pure; it melted between 144 and 152°. 
= 
x 
_ heated for 30 hours in a sealed tube with nitric acid (d 1.075) up to 145/ 150°, it formed 
- 
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: 
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addition to the two nitro-compounds, i-camphoric acid had been formed. 
derivatives; however, no trace of such an acid was to be detected. But it may be 
obtained by oxidation of the ketones derived from the nitro-compounds. When nitric acid 
E acts on isocamphane, o-nitrocamphene 4) and a mixture of secondary nitro-compounds, 
CioHiz-NOz (m. p. 48 to 49°), of butter-like consistency, are formed. On oxidation with — 
are very volatile and their smell reminds of camphor. Further oxidation leads to 
& 
___-asocamphocamphoric acid (4,4,5-trimethyleyclopentane-1,2-dicarboxylic acid), CioHieOs. 
z By the action of solid potassium hydroxide on camphenilonehydrazone (m. p. 29 
to 31°), Nametkin obtained camphenilane, CyHis, a hitherto unknown hydrocarbon; 
Nametkin, therefore, nitrated absolutely pure camphane, prepared from camphylidene- 
hydrazine according to Kishner’s process’); it melted between 157 and 158°. On being — 
It might reasonably be expected that on nitration of ssocamphane the hitherto 
_ unknown bibasic isocamphocamphoric: acid would be formed, in addition to nitro-— 
: : bene oe A. M. -Chuchrikowa, S. S. Nametkin*) investigated — 
- tertiary nitro-compounds were not obtained. The nitration of camphane (dihydro- 
Sie eseeiene) had already previously been carried out by M. Konowalow and S. Kikina?). 
~ two nitro-compounds; the a-nitrocamphane (m. p. 128 to 130°) and the isomeric 
a'-nitrocamphane (m. p. 146 to 147°). Both products are not volatile at ordinary ~~ 
temperature and resemble camphor in appearance and smell. On being oxidized with 
a 2 per cent. potassium permanganate solution at 0°, they both yielded i-camphor. ee = 
‘i 
in 
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seats 
: 
= alkaline potassium permanganate solution at 0°, 8-isocamphone, CioHisO (m. p. 91 to me 
___ 92°) and 3’-ésocamphone (m. p. 63 to 64°) form from the nitro-compounds. Both ketones 
m. p. 15 to 16°; b. p. 142.5° (753 mm.); d2> 0.8547; Npo0 1.4555. The nitration with ~ 
nitric acid (d 1.075) in a sealed tube led to 8-nitrocamphenilane, CyHis-NO2 (m. p. 18 
to 20°), f-isocamphenilone, C>HuO (m. p. 63 to 65°) and 4,4-dimethylcyclopentane- — 
1,3-dicarboxylic acid, which the authors call apofenchocamphoric acid. The acid forms _ 
a FH | ee CH CH 
jal HsC-— | CHa (HCC | CH (HsCC-—— | CH 
< C(CH2)2 CH, CH, 
Es Meee er oc. cr, cL ee 
Z C-CH; | 7 CH | CH 
3 Camphane. Isocamphane. Camphenilane. 
quantitatively on oxidation of c CH.), - CH(CO.H C(CH.)» CH(COH): 
_ f4socamphenilone. This ketone cet ae re Seeee ae aS 
___ ishighly volatile and has a feeble Fe (CHs)> Cue >: Cy: CH (COsH) 
Sa" smell recalling that of camphor. Isocamphocamphoric acid. Apofenchocamphoric acid. 
Chem. Zentralbl. 1916,-1. 884/886. — 7) Journ. russ. phys. chem. Ges. 84 (1903), 935; Chem. Zentralbl. 1903, 
+, 513. — %) See Report April 1912, 195. 4) See Report October 1918, 133. 
a in ; a g* 
Idi Bias phys. kgm Sot. 42 (1915), 405, 409, 414, 425; Journ. chem. Soc. 108 (1915), 698/701. — 
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