Phenyliodide Chloride and Iodosobenzene Acetate. 549 
and 
c/ 
COO Et 
/Cl Na x COO Et 
2C S H, — K +2 )C< = 2C 6 H,I + INaCl + 
X C1 Na/ x COO Et 
C: 
COO Et 
COO Et 
^COO Et 
Should the second of these reactions take place, then the 
action of phenyliodide chloride is exactly analogous with that of 
incline on the sodium compounds of malouic ester as found by 
Bischoff and Bach (B. 17-2781; B. 291290; B. 32*860). 
The experiments were performed both at ordinary temperatures 
and at the temperature of the boiling water-bath. In each case the 
reactions appeared to go in the same way, although more readily 
at the higher temperatures. 
The attempt to isolate bodies in which the iodine was tri valent, 
proved futile, although the methods of separation employed may 
account for the failure of the experiments. 
Three methods of separation were tried : the first being the 
fractional distillation of the reaction mixture under reduced 
pressure, after Kitering off the precipitate formed; the second 
being to pass steam through the reaction mixture and then to 
extract the residue with ether; and the third was to extract the 
cold reaction mixture with ether. 
The results of these three methods were as follows : 
(1) Three fractions were collected consisting of 
(а) alcohol and ether, 
(б) phenyliodide, 
and (c) a substance containing no iodine. 
Only a small quantity of (c) .could be collected owing to 
excessive charring and decomposition taking place. 
(2) Phenyliodide distilled over leaving a residue containing 
no iodine, and 
(3) The extract contained much phenyliodide. 
The high temperatures employed in ( 1 ) and (2) would doubt- 
less tend to affect the decomposition of any substance containing 
the groupings 
m C— I = C= or — C— I— C— , 
but the third method proved also that at ordinary temperatures 
phenyliodide was formed, so that the reactions under the con- 
36—2 
