DE. A. W. HOFMANN ON THE PHOSPHOEHS-BASES. 
517 
ammonium to the action of triethylpliospliine : 
[(C^ H, Br) (C, H ,)3 P] Br + (C H 3)3 N = [(C^ Br) (C 11,), N] Br + (C, H 3)3 P 
H f(C2H,)3P7' 
{^ 2 ^ 4 ) (CH3)3 Nj 
The bromide of bromethylated trimethylammonium is indeed readily attacked by 
triethylphosphine, but the change is very different from what I had expected. I intend 
in another paper to return to the products of this reaction. 
Before lea\ing the history of the phosphammonium-compounds, I have briefly to 
allude to a peculiar deportment of the bromethylated bromide. When treating this 
compound with triethylamine instead of trimethylamine, expecting, of course, to observe 
a repetition of the phenomena so frequently witnessed, I was surprised to find that these 
substances, although acting with considerable energy, fail to produce the anticipated 
phosphammonium-compound. This unforeseen result induced me to examine this reaction 
repeatedly and with particular care. The result remained the same. On evaporating 
the alcoholic product of the reaction, and treating the concentrated solution with oxide 
of silver, a powerfully alkaline hquid remained, even after the expulsion of the triethyl- 
amine, considerable quantities of which were liberated. This residuary alkaline liquid, 
saturated with hydrochloric acid, yielded, on addition of dichloride of platinum, the 
beautiful octohedra of the oxethylated triethylphosphonium-platinum-salt, which was 
identified by analysis. The specimen which was employed in analysis IV., mentioned in 
the description of the oxethylated platinum-salt, had been prepared by the action of tri- 
ethylamine on the bromethylated bromide : 
[(C, Br) (C^ HJ 3 P] Br + (C^ N + O = [(C, 0) (C, P] Br + [(C, HJj H N] Br. 
This equation involves the intervention of water in the reaction, which Avas obviously 
furnished by the imperfectly de-hydrated alcohol used in the experiments. In the 
anhydrous state, the bromethylated bromide and triethylamine scarcely act at 100 °; 
between 120° and 130°, a reaction takes place, among the products of which, as yet very 
imperfectly examined, I was likewise unable to trace the presence of a phospham- 
monium-like compound. It can scarcely be doubted that this reaction gives rise to the 
formation of bromide of vinyl-triethylphosphonium : 
[(C., H, Br) (C^ Hj), P] Br + (C, H,), N = [(G, H.,) (C, H,), P] Br + [(C, H N] Br. 
Experimentally the question remains undecided. 
The elegance and precision with which the bromethylated bromide fixes the elements 
of ammonia and of the monamines, very naturally suggested the idea of examining the 
deportment of this body uuder the infiuence of diamines and triamines. The results 
obtained in these experiments do not belong to this part of the inquiry. Suffice it to 
say for the present, that these substances attack the bromide with the utmost energy, 
giving rise to an almost unlimited number of polyatomic bases of a higher order, the 
