1869.] On Et hylic Mustard-oil and Stclp ho cyanide of EthijL 269 



II. " Compounds Isomeric with the Sulphocyanic Ethers. — III. 

 Transformations of Ethylic Mustard-oil and Sulphocyanide of 

 Ethyl." By A. W. II of mann ^ Ph.D., M.D., LL.D., F.ll.S. 

 Received November 19, 1868. 



In the present paper I beg leave to communicate to the Royal Society 

 some experiments made for the purpose of testing the views which I have 

 lately* advanced respecting the constitution of the mustard-oils and the 

 sulphocyanic ethers isomeric with them. These experiments were exclu- 

 sively performed in the ethyl-series. Not only is ethylamine much more 

 readily prepared than the methyl-base, but the elucidation of the meta- 

 morphoses examined was not unfrequently facilitated by the selection of 

 compounds for the construction of which the material had simultaneously 

 been taken from the monocarbon- and dicarbon-series. 



Action of Hydrogen in condicione nascendi upon Ethylic Mustard-oil. 



I have, in the first place, examined this reaction, because experiments 

 performed by M. Oeserf have already supplied some information on the 

 behaviour of allylic mustard-oil under analogous conditions. 



On adding zinc and hydrochloric acid to an alcoholic solution of ethylic 

 mustard-oil an evolution of sulphuretted hydrogen becomes at once percep- 

 tible ; it soon diminishes, but continues for several days. In the several 

 stages of this process the gas evolved was examined for carbonic acid ; but 

 not a trace of this gas could be detected. As soon as the evolution of sul- 

 phuretted hydrogen has ceased, the liquid is found to contain a large 

 quantity of fine white needles ; when submitted to distillation, it yields the 

 same body, which, passing over with the vapour of water and alcohol, col- 

 lects in the form of white crystals upon the water in the receiver. If the 

 residue be now allowed to cool, an additional quantity of the crystalline 

 compound is deposited. Analysis and examination of the properties of these 

 crystals have identified them with the substance generated by the action 

 of sulphuretted hydrogen upon methylic aldehyde J, to which I assigned 

 the formula 



CH 2 S, 



stating at the same time that a higher molecular weight might possibly be 

 found to belong to this sulphaldehyde of the methyl-series. 



On adding strong soda-lye to the liquid containing chloride of zinc, from 

 which the crystals have been separated, until the oxide at first precipitated 

 is redissolved, a strongly alkaline layer collects on the surface of the solu- 

 tion, which may be considerably augmented by the intervention of a small 

 quantity of alcohol. This layer was removed and separated from adhering 

 soda by distillation. When the very volatile distillate was saturated with 



* Proceedings, vol. xvii. p. 67. 



f Ann. Chem. Pharm. vol. cxxxiv. p. 7. 



t Proceedings of the Boyal Society, vol. xvi. p. 156. 



X2 



