118 Report of Schimmel $ Co. 1921. 



The glucosides which are contained in the root of the primrose (Primula offici- 

 nalis, Jacq.), primverin and primulaverin 1 ), are hydrolysed by a ferment called prim- 

 verase into the ^-methylether of /?-resorcylic acid or into the same body and into 

 m-methoxysalicylic methylester (on the one hand) and into a biose (on the other). This 

 sugar, which A. Goris and Ch. Vischniac 2 ) styled primverose, has further been in- 

 vestigated by the same authors. Primverose is soluble in water, in 80 per cent, alcohol 

 and in methylalcohol, melts in the "bloc Maquenne" at 209 to 210°, has initially the 

 specific optical rotation [«] D + 22.70°, and after 24 hours [«] D — 3.43°, reduces Fehling's 

 solution and forms an osazone (m. p. in bloc Maquenne 224 to 226°). The biose is 

 composed of one molecule each of dextrose and xylose. 



Nitrogenous Bodies. 



s 



In a paper on q/cfohexylamine A. Skita and H. Rolfes 3 ) describe among other 

 methods the following for the preparation of cyclohexyl mustard oil: — 



1. N : N'-diq/cfohexylthiocarbamide (I), m. p. 180 to 181°, obtained from c^/c/ohexamine 

 and carbon disulphide, was distilled with glacial phosphoric acid. The distillation 

 product, q/c/ohexyl-isothiocyanate C 6 HuN : C : S (II), a liquid having a stinging smell of 

 mustard oil, boiled at 219° (746 mm). 



CS<^ — > C 6 H lt N : C : S + C«HuNH 8 



NH-C 6 Hn (II ) cyclohexyl- CyeJohexylamine. 



(I) N : N '-Dicydohexylthiocarbamide. /sothiocyanate. 



2. The same body was obtained with a better yield by the Hofmann mustard-oil 

 synthesis, by the action of mercuric chloride upon ammonium dicycZohexyl-dithiocar- 

 bamate (III), the first reaction product of carbon disulphide and ci/cfohexylamine. 



/NH-CeHu 

 CS< — > C«HnW : C : S + H 2 S + C 6 H U -NH 2 



X S-NH 3 C 6 H U 



(III) Dicf/cZohexyldithiocarbamate of ammonium. 



The cyclohexyl-isothxo cyan ate, the fist representative of the hydroaromatic mustard 

 oils is, like the aliphatic and aromatic mustard oils, highly reactive and forms with 

 alcohols and phenols easily thiourethanes and, with ammonia and amines, thio- 

 carbamides. 



Referring to this work of Skita and Rolfes, J. von Braun 4 ) points out that primary 

 amines containing a non-aromatically bound NH 2 -group are most easily transformed 

 into the corresponding mustard oil by means of the thiuramdisulphide method. Braun 5 ) 

 and also W. Schneider 6 ) proved years ago that this method is particularly suitable 

 for the preparation of fatty-aromatic, hydroaromatic and complex aliphatic mustard 

 oils. The cyclohexyl mustard oil described by Skita and Rolfes could also be obtained 

 from hexahydroaniline in a few minutes with almost theoretical yield. 



In continuation of two previous researches, in which Rupe reported on the conden- 

 sation of hydroxymethylene-camphor with various bases concerning stereo-isomerides 

 of aminomethylenecamphor, H. Rupe and W. Kussmaul 7 ) attempted to prepare the reduced 



*) Cf. Gildemeister and Hoffmann, The Volatile Oils, 2 nd ed., vol. Ill, p. 391. — 2 ) Bull. Roure-Bertrand 

 Fils, April 1920, 7. — 3 ) Berl. Berichte 53 (1920), 1242. — *) Berl. Berichte 53 (1920), 1588. — B ) Cf. Report 

 October 1912, 164. — 6 ) Cf. Report April 1915, 108. — 7 ) Helvet. chim. acta 3 (1920), 515. 



