P — 167 — 



alcoholic solution by Paal's method. Singularly enough the hydrogenation 

 does not result in the familiar pinocamphone oxime, but in its isomeride, 

 m. p. 87°. When this isomeric pinocamphone oxime is reduced with 

 acids only a portion of it returns to the ketone. The semicarbazide of this 

 ketone melted at 208° and suffered no depression of m. p. with pino- 

 camphone semicarbazone. 



G. Cusmano, in collaboration with A. Linari 1 ), has continued his pre- 

 vious investigations into the action of hydroxylamine upon the nitroso- 

 chlorides 2 ). By acting with hydroxylamine upon «-terpineol nitrosochloride 

 the authors obtained the o-hydroxylamine oxime of «-terpineol (m. p. 183° 

 with decomp.) which, upon treatment with nitrous acid, gives rise to the 

 corresponding (Msonitramine oxime (m. p. 156 to 157° with decomp.). The 

 latter, when heated upon the water-bath, yields the oxime C10H17MO2. 

 Treatment with acids does not hydrolyse this oxime, but causes ring- 

 formation, a ketone CioHi 6 2 , possessing a faint odour of cineol, being 

 generated. This ketone yields a semicarbazone, m. p. 220°. When oxidised 

 with potassium permanganate in 1 p. c. sulphuric acid it gives rise to the 

 methylketone of homoterpenylic acid Ci Hi 6 O 3 . Oxidation of the ketone 

 with permanganate in alkaline solution yields, after a considerable interval, 

 cineolic acid in addition to the methylketone. 



CH 3 

 O C 



H 2 cl JcH 2 



CH 

 C(CH 3 ) 2 . 



Ketone Ci H 16 O 2 . 



*) Gazz. chim. ital. 42 (1912) I. 1. Quoted from Chem. Zentralbl. 1912, I. 1012. 

 *) Gazz. chim. ital. 40 (1910) II. 122. See also Report October 1910, 178. 



