m — 165 — 



The author has prepared the following: 



Phenylethyl mustard oil, C 6 H 5 (CH 2 ) 2 N : CS. A water-white liquid with 

 an odour of Spanish radish. B. p. 141 to 144° (11 mm.). With ammonia 

 it gives rise to a thio-urea, m. p. 137°. 



Phenylpropyl mustard oil, C 6 H 5 • (CH 2 )3 ■ N : CS. A water-white liquid 

 which, when left standing for a considerable time, turns cloudy with 

 decomposition. Odour resembling that of Spanish radish, but fainter than 

 that of No. 1. B. p. 156 to 160° (12 mm.), not without decomposition. With 

 ammonia it gives rise to a thio-urea, m. p. 111°. 



Phenylbutyl mustard oil, C 6 H 5 (CH 2 )4N : CS. A liquid as clear as 

 water and without any pronounced odour. When left standing it decom- 

 poses, sulphur being separated out, and acquires a disagreeable odour. 

 B. p. 166 to 174° (12 mm.) not without decomposition. With aniline it 

 affords phenyl phenylbutylthio-urea, m. p. 95°. 



Benzohydryl mustard oil, (C 6 H 5 ) 2 CH-N : CS. Crystals with m. p. 50° 

 (from ether - light petroleum). Practically odourless, with a faint odour of 

 mustard when in the melted state. With aniline it gives rise to benzo- 

 hydryl phenylthio-urea, m. p. 181°. 



Anisyl mustard oil, CH 3 0-C 6 H 4 CH 2 N:CS. A colourless oil with a 

 faint odour. B. p. 170 to 175° (16 mm.). With aniline it gives rise to 

 anisyl phenylthio-urea, m. p. 142°. 



As mentioned in our last Report (p. 195), N. Kishner has resolved 

 hydrazine compounds into hydrocarbons and nitrogen by boiling them 

 with solid potassium hydroxide. In conjunction with A. Sawadowski 1 ) the 

 author has continued his previous researches, and has investigated the 

 action of hydrazine upon pulegone. When pulegone hydrazine (b. p. 131 

 to 132° at 23 mm.; [«] D — 5,55°) is distilled with solid potassium hydroxide 

 there results a hydrocarbon CioH i8 , known as carane: b. p. 169,5°, d^ 0,841 1, 

 [«] D + 57,64°, n D 1,4567 which, when treated in the cold with fuming hydro- 

 bromic acid, yields a bromide Ci H 19 Br. When this bromide is heated 

 with alcoholic potash liquor the result is m-zl 3(8) -menthene: b. p. 172,5 

 to 174,5°, d^ 0,8247, n D 14577. Oxidation of this hydrocarbon with potas- 

 sium permanganate yields methylq/cfohexanone and /?-methyladipic acid. 

 When the bromide is heated with aniline the result is m-zl 8(9) -menthene 

 ► (b. p. 171 to 172°; d^ 0,8194; [«] D + 3,99°; n D 1,4580). Repeated treatment 

 with hydrobromic acid and distillation with aniline cause an increase of 

 rotation, hence it is probable that the resultant compound consists of a 

 mixture of m-zl 3C8; - and m-zl 8(9) -menthene. Oxidation with potassium per- 

 manganate solution yields methylc^/dohexanone, together with i- and d- 

 methyladipic acid. <d 8(9) -Menthene, with fuming hydriodic acid, yields an 



l ) Journ. russ.phys. chem. Ges. 43(1911), 1132, 1157, 1398. Quoted from Chem. Zentvalhl. 

 1912, I. 1456, 1457, 1622. 



