550 Mr Hodgson, Some Reactions of 
ditions employed evidently tend to take place in the second way 
depicted above. 
The same experiments were performed with iodoso-benzene 
acetate and similar results established, although the yields were 
better than when using phenyliodide chloride. 
The same experiments were also performed using diphenyl- 
iodonium iodide, both at ordinary temperatures and by heating for 
several hours on the boiling water-bath, but in this case no 
chemical reaction appeared to take place. 
The reactions proceeded in exactly the same manner when 
sodium cyanacetic ester was acted on by phenyliodide chloride 
and by iodoso-benzene acetate, phenyliodide being produced and 
dicyansuccinic ester formed as follows : 
Cl CH. Na. CN. COO Et 
C 6 H 5 — 1< + - C 6 H 5 I + 2NaCl + CH . CIST . COO Et 
X C1 CH . Na . CN . COO Et | 
CH . CN . COO Et 
and 
OOC . CH, CH . Na . CN . COO Et 
C 6 H 5 — 1< + = C 6 H 5 I + 2CH 3 . COO Na 
x OOC . CH 3 CH . Na . CN . COO Et 
+ CH . CN . COO Et 
I 
CH . CN . COO Et 
Experimented. 
The phenyliodide chloride was prepared by passing chlorine 
into a mixture of phenyliodide dissolved in five times its volume of 
chloroform, and cooled by ice-water. The yellow needles which 
separated were well washed on a filter-paper with pure chloroform, 
and allowed to dry in the air on a pad of filter-paper. 
Action of phenyliodide chloride on mono-sodium malonic ester. 
(a) At ordinary temperatures. 
Mono-sodium malonic ester was prepared by dissolving 
2*5 1 grams of sodium wire in absolute alcohol, and then adding 
17 '45 grams of malonic ester to the solution. After standing 
a short time, dry ether was added to the mixture until turbidity 
just commenced, 15 grams of C 6 H 5 IC1 2 were then added gradually 
and the mixture well shaken ; heat was developed and moderated 
by cooling the vessel. The mixture was allowed to stand for 
a day and then the alcohol and ether distilled off at ordinary 
atmospheric pressure. 
On raising the temperature, phenyliodide distilled over be- 
