46 
Proceedings of the Royal Society 
suffering dissociation into trimethylamine and a derivature of acetic 
acid, or simply volatilizing without change. 
The predictions of Dr Crum Brown and the author have thus been 
verified. 
5. On the Action of Haloid Compounds of Hydrocarbon Radi- 
cals on Phosphide of Sodium and on the Salts of Tetra- 
Benzyl-Phosphonium. By Professor Letts and N. Collie, 
Esq. 
(4 bstract . ) 
The difficulty of preparing tertiary phosphines either by heating 
alcohols with phosphonium iodide or by acting on zinc ethers with 
terchloride of phosphorus, of which we have had much experience, 
induced us to seek for other and less troublesome methods for obtain- 
ing these bodies in considerable quantity. 
The ease with which phosphorus combines with certain metals, and 
the readiness with which the resulting compounds react on haloid 
ethers of hydrocarbon radicals led us to think that, if only com- 
paratively pure metallic phosphides could be obtained by a simple 
process, we should have no difficulty in preparing the tertiary 
phosphines and phosphonium compounds. 
This is no new notion, — all the earlier experiments* to obtain phos- 
phines having been made by the action of metallic phosphides on the 
chlorides and iodides of hydrocarbon radicals. Hofmann employed 
sodium phosphide, but eventually gave up the method on account of 
the uncertainty of the reaction, the frequent explosions in operating 
on the phosphide of sodium, and the great difficulties experienced 
in separating the resulting phosphines from each other, “ not to 
speak of the difficulty of obtaining the phosphide of sodium fit for 
the reaction.” 
In experiments which we have made with this method in the ethyl 
and benzyl series we have not experienced the difficulties of which 
Hofmann and others speak. 
* Taul Thenard, “ Compt. Rend.,” xx. 144, and xxv. 892; Berle, “ Journ. 
fiirprak. Chem.,” 66, 73 ; Cali ours and Hofmann, “ Ccmpt. Rend.,” xli. 813 ; 
Drechsel and Finkelstein, “ Ber. dent. Chem. Ges.,” iv. 352. 
