— 171 — 



and an aldehyde C9H15CHO. The chloroketone proved to be a hitherto 

 ^jnknown chlorocamphor, of which the semicarbazone melted at 234 to 235°, 

 and yielded camphoric acid when oxidised with permanganate of potassium, 

 and camphor when heated with alcoholic potash liquor in a sealed tube 

 at 150 to 160°. The aldehyde C 9 H 15 CHO could be purified from the 

 primarily produced bisulphite-compound, and was identified as campheni- 

 lanic aldehyde. This aldehyde being a true camphene derivative, its gene- 

 ration from bornylene points to the relationship of this hydrocarbon with 

 camphene. When exposed to air, camphenilanaldehyde was oxidised to 

 a mixture of camphenilanic acid (m. p. 65°) and isocamphenilanic acid 

 (m. p. 118°). Camphenilanic acid is very readily converted into the iso- 

 modification, repeated recrystallisation from water, alcohol or light petro- 

 leum being sufficient to effect the conversion. When semicarbazide is 

 allowed to act upon camphenilanaldehyde, ^ocamphenilanaldehyde semi- 

 carbazone (m. p. 191 to 192°) is formed. Bromoisocamphenilanic acid 

 (m. p. 204 to 205°) was prepared by the authors by heating isocamphe- 

 nilanic chloride with bromine under pressure, and decomposing the bromi- 

 nated chloride with water. Heating brormsocamphenilanic acid with aqueous 

 soda solution gave rise to an unsaturated acid C9H13XO2H (m. p. 147°). 

 Henderson and Heilbron also acted with nitrous acid upon bornylene, 

 by overlaying concentrated aqueous sodium nitrite solution with a solution 

 of bornylene in light petroleum, and gradually adding glacial acetic acid. 

 They obtained the following reaction-products: 1. Bornylene nitrosite 

 (CioHi 6 N 2 03)2, m. p. 163°, which was oxidised into camphoric acid. 2. An 

 oily liquid, perhaps bornylene isonitrosite. 3. Camphorquinone (m. p. 197 

 to 198°) and 4. a crystalline body, m. p. 84 to 85°, perhaps a bornylene 

 nitrite. With nitric acid, bornylene was oxidised into a mixture of cam- 

 phoric acid and a body CioHi60 4 N 2 , crystallising in yellow needles, which 

 was identified as to be a dinitrocamphane. 



The bornylene employed for these reactions was prepared by Tschugaeffs 

 method from borneol from primarily-produced bornyl methylxanthogenate- 



On the constitution of D-Z-fenchene see p. 169. 



«-Pinene. Mario Mayer 1 ) has published an historical resume of the 

 researches into pinene, and of the relations of pinene to camphor and to 

 other bodies of similar chemical structure. From its nature it follows 

 that the publication is chiefly retrospective and that the new experimental 

 rr jfcerial contained in it is of subordinate interest, the principal reference 

 of this character being that dealing with the splitting-up of the hydroxyl- 

 amine oxime of Z-«-pinene by means of «-bromo-^-camphor sulpho-acid. 



*) Test di libera docenza, R. Institute di Studi sup., Florence 1911. Our best thanks 

 are due to the author for kindly sending us a copy of the pamphlet. 



