Action of Iodacetic and of Bromacetic Ethyl Ether on Sulphide of Methyl. 
By Dr E. A. Lerts. 
(Sent for Publication August 19, 1878.) 
Among other experiments which were tried before the compounds of 
dimethyl-thetine had been investigated, was the action of iodacetic ethyl ether on 
sulphide of methyl, as it was thought that these two substances would yield an 
addition product more readily than bromacetic ethyl ether and sulphide of 
methyl. It was found, however, that the reaction took quite a different course 
—iodide of trimethyl-sulphine bemg produced in abundance.* 
It seemed highly interesting to submit this reaction to a closer investiga- 
tion, especially after the experiments on the action of bromacetic acid on 
hydrocarbon sulphides had shown that the bromine of the one and the sulphur 
of the other simply change places. It appeared to me to be of importance to 
ascertain whether the reaction in question was of a similar nature. 
The iodacetic ethyl ether employed in these experiments was prepared 
from chloracetic ethyl ether by acting on it with iodide of potassium. Rather 
more than the equivalent quantity of the latter was dissolved in as small a 
quantity of water as possible, the solution largely diluted with alcohol, then 
mixed with the chloracetic ether, and the whole distilled from a water bath 
till no more liquid passed over. The residue in the retort was then mixed 
with water, and the crude iodacetic ether (which was always brown from the 
presence of free iodine) first decolorised with hyposulphite of soda solution 
and then washed with water. 
A great many experiments were made with the iodacetic ethyl ether thus 
prepared and sulphide of methyl. The following is a summary of the method 
of investigation pursued, and of the results obtained :— 
When iodacetic ethyl ether and sulphide of methyl are mixed, a reaction 
occurs almost immediately,—free iodine separates, colouring the solution brown, ~ 
and soon dense oily drops collect. The reaction is so energetic, that, unless 
checked by immersing the vessel in which the experiment is made in cold 
water, the temperature may rise sufficiently high to cause the sulphide of 
methyl to boil off. The oily drops gradually accumulate to a layer of liquid 
which sinks to the bottom of the vessel. On leaving the whole to itself for 
a night, this oily layer is found to have solidified to a mass of crystals—in fact, 
the whole product is almost solid. 
* “« Proceedings,” 1873-1874, p. 220. 

