- 166 — f 



iodide from which upon boiling with alcoholic potash liquor /4 8(8) -menthene 

 results. When carane is reduced by Sabatier's method, and also when 

 the iodide from zl 3C8) -menthene is reduced with hydriodic acid at 200°, 

 w-menthane, Ci H 20 , is produced. The iodide from J 8(9) -menthene, when 

 reduced with hydriodic acid, is likewise converted into a hydrocarbon 

 C10H20. 



In glacial acetic acid solution, carane readily absorbs bromine; the 

 resulting bromide, when treated with quinoline, yields a menthadiene Ci Hi 6 . 



Kishner has also described a few conversions of thujane. For the 

 preparation of pure thujane, thujylidene hydrazine in alcoholic solution 

 is reduced with sodium amalgam, after which the crude thujylamine is 

 oxidised with potassium ferricyanide. The thujane possesses the following 

 constants: b. p. 157 to 157,5°, d^ 0,81 71, [«] D + 62,29°, n D 1,4412. With 

 fuming hydrobromic acid thujane yields a compound Ci Hi 9 Br which is 

 capable of being reduced into a hydrocarbon Ci H 20 . When the bromide 

 is distilled with quinoline the result is a hydrocarbon Ci Hi 8 (b. p. 162 to 164°). 

 The thujane further yields an unstable bromide Ci Hi 9 Br from which likewise 

 a hydrocarbon Ci Hi 8 results, as well as an iodide which, when reduced, 

 also leads to a hydrocarbon Ci Hi 8 . The thujane also forms a dibromide 

 CioHi 8 Br 2 , which when boiled with alcoholic potash liquor yields a hydro- 

 carbon CioHi 8 . 



From ionone and pseudo-ionone also, the corresponding hydrocarbon 

 is readily obtainable. In order to accomplish this a mixture of 25 g. ionone 

 in alcoholic solution is boiled for 5 hours with 25 g. 50 p. c. hydrazine 

 hydrate, after which the oil is distilled off from an oil-bath until the 

 thermometer indicates 160°. The residue, which represents the hydrazine- 

 compound of the ionone, is dried with potash under heat and then 

 reduced with solid potassium hydroxide, in the course of which treatment 

 «-ionane, Ci 3 H 22 , distils over: b, p. 220 to 221°, d^ 0,8530; n D 1,4784. The 

 yield amounts to 20 g. «-Ionane constitutes a liquid with an odour resemb- 

 ling that of turpentine. In the same manner pseudo-ionone yields pseudo- 

 ionane (b. p. 224 to 225°; d^ 0,8151; n D 1,4725); when boiled in a glacial 

 acetic acid solution in the presence of 2,5 p. c. sulphuric acid pseudo- 

 ionane is converted into et-ionane. 



Kishner 1 ) also describes the conversion of carone into carane. He 

 heated carylidene hydrazine (from carone and hydrazine hydrate) with solid £ 

 potassium hydroxide, when 1-carane (b. p. 169 to 169,5°; [«] D — 47,06°) 

 was formed. 



According to O. Wallach 2 ) the direct conversion of nitrosopinene into 

 pinocamphone oxime can be attained by reducing nitrosopinene in methyl- 



*) Journ. russ. phys. chem. Ges. 43 (1912), 1554. Quoted from Chem. Zentralbl. 1912, I. 1713. 

 2 ) Liebigs Annalen 389 (1912), 185. 



