86 PROCEEDINGS OF THE AMERICAN ACADEMY. 



carbonic disulphide, and is almost insoluble in ligroin. It is very 

 sparingly soluble in boiling water, and is deposited in the form of fine 

 needles as the solution cools. From chloroform it crystallizes in clear 

 flat prisms, which melt quite sharply at 183°, although decomposition 

 sets in at a somewhat higher temperature. Toward alkalies it behaves 

 like the corresponding bromine derivative. It dissolves more freely in 

 dilute sodic hydrate on heating than in water, and, if this solution is 

 quickly cooled, it crystallizes out apparently unchanged. On longer 

 heating decomposition ensues with the formation of phenylisocyanide. 



Action of Hydriodic Acid. 



The action of hydriodic acid upon the aj3-dichlorcrotouolactone we 

 have studied only so far as to prove that a-iod-/3-chlorcrotonolactone 

 is formed. This body we have also made directly from mucochloryl- 

 bromide by the action of hydriodic acid at 100°. In order to keep 

 up the strength of the hydriodic acid we found it advantageous to add 

 at the same time potassic iodide and red phosphorus. The product 

 was precipitated by the addition of water decolorized with sulphurous 

 acid and recrystallized from alcohol. 



0.2015 grm. substance gave 0.3116 grm. AgCl + Agl. 



Calculated for C 4 H 2 C1I0 2 . Found. 



Cl+I 66.45 66.36 



a-Iod-/3-chlorcrotonolactone dissolves very readily in benzol, is 

 freely soluble in ether, but is more sparingly soluble in chloroform 

 or carbonic disulphide. It dissolves easily in hot alcohol, but as this 

 solution cools the greater part separates in long flattened needles 

 which melt at 108-109°. In its behavior toward reagents it closely 

 resembles the bodies of similar constitution already described. 



/3-Chlorcrotonolactone. 



By the action of zinc dust and glacial acetic acid the a/3-dichlor- 

 crotonolactone may be reduced without difficulty to the /3-chlorcro- 

 tonolactone, but the physical properties of the latter body make 

 its isolation a little more troublesome than that of the corresponding 

 body containing bromine. We dissolved the dichlorcrotonolactone in 

 nearly twice its weight of 80 per cent acetic acid, and slowly added 

 with cooling somewhat more than the theoretical quantity of zinc 

 dust. The reduction was at first attended with the evolution of 

 heat, but afterward became sluggish. After standing over night, the 



