— Ill 



of pinene nitrolbenzylamine, nitrolpiperidide, and nitrosocyanide, from 

 which it would appear that these compounds are monomolecular. The 

 nitroso-group in these compounds assumes an isonitroso or oxime structure. 



Camphene. G. Wagner, St. Moycho, and F. Zienkowski 1 ) 

 report on some experiments made to clear up the constitution of 

 camphene. In continuation of earlier experiments by Wagner, the 

 authors have submitted comparatively large quantities of pure camphene 

 to oxidation with potassium permanganate. At ordinary temperature 

 the action of I per cent, and 4 per cent, solutions of permanganate 

 (1 atom oxygen to 1 molecule camphene) proceeds but very slowly. 

 Comparatively many neutral and only few acid products are formed, 

 and the bulk of the camphene remains unattacked. More rapid and 

 complete is the oxidation with 4 per cent, permanganate solution 

 (3 atoms oxygen to 1 molecule camphene) at 6o°. Qualitatively the 

 same products are formed, but the proportion of the acid and neutral 

 constituents is reversed. In addition to the already known oxidation 

 products: camphenylone C 9 H 14 O, campheneglycolC 10 H 18 O 2 , camphene- 

 camphoric acid C 10 H 16 O 4 , and camphenylic acid C 10 H 16 O 3 , a neutral 

 compound C 16 H 10 O 2 of the melting point 169 to 170 was isolated 

 (from ether-ligroin). The nature of this compound has not yet been 

 cleared up. On oxidation with permanganate there are formed one 

 ketone, whose semicarbazone melts at 184,5°, and two acids C 10 H 14 O 3 , 

 melting point 197 to 198°, and C 10 H 16 O 4 , melting point 203°. As the 

 oxidation-products differ from those of camphene glycol, the two com- 

 pounds appear to have totally different constructions. For pure camphene- 

 glycol, the melting point 199° to 200° was ascertained. During the 

 treatment of camphene with permanganate, a small portion escapes 

 oxidation. After suitable purification, a hydrocarbon C 10 H 16 was isolated 

 from it, which had the following constants: melting point 67,5° to 67,8°; 

 boiling point 152° to 153° (757,5 mm. pressure). It appears to be 

 identic with Wagner and Godlewski's cyclene. 



In order to verify the correctness of Wagner's 2 ) formulae for 

 camphenylone (I) and isoborneol (II), Tschugaeff had attempted to 

 obtain isoborneol by the action of magnesium and methyl iodide on 

 camphenylone 



(I) 4r CH 2 -^ (II) ^- CH 2 -^ 



O (CH 3 ) 2 OH.CH3 (CH 3 ), 



but he had thereby found that the alcohol which is formed during 

 this reaction, is not identic with isoborneol. According to tests by the 



x ) Berl. Berichte 37 (1904), 1033. 



2 ) Journ. russ. phys.-chem. Ges. 29 (1897), 121. 



