ACTION OF PHOSPHIDE OF SODIUM ON HALOID ETHERS. 209 
Sulphuretted Compound.—When the phosphine oxide is fused with sulphur 
a reaction occurs, which apparently varies with the temperature and with 
the quantity of sulphur employed. Jf much sulphur is taken and the mixture 
heated to a high temperature, sulphuretted hydrogen is evolved, the mass 
becomes dark coloured, and resinous products are formed. 
But if the proportion of sulphur is low (P(C,H,),0 :S,) and the temperature 
is kept at the melting point of the oxide or rather higher (240°), the sulphur 
dissolves, no gas is evolved, and the product dissolves completely in a large 
quantity of boiling alcohol. The solution on cooling deposits beautiful silky 
needles of a light buff colour, which do not readily change in appearance (nor 
alter in their melting point) by recrystallisation. That the new substance 
contains sulphur is shown by burning it on platinum foil, when a strong odour 
of sulphurous anhydride is at once observed. 
The substance fuses at 211°-212° (uncorrected). It is insoluble in water, 
and sparingly soluble in alcohol. The only determinations made were of the 
carbon and hydrogen which it contains. 
0:2103 gave 0:597 CO, =0:16254 C =77°3 per cent. 
02103 ,, 0132 H,O=0:01466 H= 6:9 * 
These numbers do not agree with any simple addition product. The only 
probable formula which agrees with the numbers obtained is, 
4 {(C;H;)sPO}, (C;H;);,POS=5 {(C;H,),PO},S. 
Thus— 
Obtained. Calculated. 
Carbon, ; : ; (TS ; : : To 
Hydrogen, . _ ‘ 6:9 4 : ‘ 6-4 
Examination of Residue, soluble in Chloroform and Alcohol only. 
This portion of the residue was contained in the dark brown mother liquors 
of the crystalline substance, which the preceding experiments have shown was 
oxide of tribenzyl-phosphine. 
On evaporating off the alcohol a dark brown syrupy mass remained, which 
solidified on cooling to a resin. This contained some crystalline matter, which 
we could not succeed in separating. We have subjected the resin to many 
experiments with the view of obtaining definite products, only, however, with 
partial success. 
In one of our earlier experiments we subjected it to the action of heat. 55 
grms. were heated in a distilling flask. The thermometer rose rapidly to 
380°, and a small quantity of a solid substance distilled. The temperature 
then fell suddenly, and a liquid distillate was obtained. After some time the 
temperature again rose above the boiling point of mercury, and the residue 
began to char. The products of this distillation were collected together and 
