20 ART. U. T. SUZUKI : THE OXIMES AND 



on heating. It may be that the oxime forms an unstable am- 

 monium salt, which soon decomposes into the sulphinic acid, 

 nitrogen and water. The similarity of the reaction makes it 

 probable that the sulphoximes are the substitution products of 

 nitrous acid and not of hydroxylamine. The difficulty of their 

 hydrolysis into hydroxylamine and the corresponding sulphonic 

 acid seems to support this view. 



When m-benzenedisulphoxime was ti-eated with fuming nitric 

 acid, it dissolved to some extent. On diluting the solution with 

 water the oxime was reprecipitated unchanged. But when the 

 nitric solution was allowed to stand for four or five days the 

 colour of the fuming nitric acid had faded a little, and small 

 crystals made their appearance on the surface of the liquid and 

 on the sides and bottom of the vessel. The crystals dissolved 

 readily in water, and the solution behaved as that of an acid. 

 Oil neutralisation with caustic soda, a crystalline precipitate of 

 a difficultly soluble sodium salt was formed. This precipitate 

 was collected, recrystallised from hot water, and analysed. The 

 amount of water of crystallisation, sodium, nitrogen, and sulphur 

 found, as well as the form of the crystals, left no doubt as 

 to its identity wdtli the sodium salt of m-benzenedisulphimide. 

 The formation of tlie imide in this case was, indeed, a surprise, 

 and it was thought possible that the crystals first formed in 

 fuming nitric acid might have been a complex compound, which 

 gave rise to the imide on hydrolysis. In order to settle this 

 point the crystals were dried upon a porous tile, then in a 

 desiccator containing strong sulphuric acid and caustic soda, and 

 a weighed quantity of the substance was titrated with tn N 

 soda solution. The titer agreed exactly with that calculated 



