146 PROCEEDINGS OF THE AMERICAN ACADEMY. 



but has not yet been studied sufficiently to determine its constitution with 

 certainty. We shall therefore content ourselves with saying that a sub- 

 stance with the formula given above could be easily derived from the 

 oxide with the ortho attachment by the action of hydriodic acid. 



In the foregoing discussion of the formulas of the oxide, the arguments 

 were based in large part upon the product obtained from it by the 

 action of isoamylamine, and it is necessary, therefore, here to give our 

 proofs of the constitution of this body. Its analysis led to the formula 

 C6Cl2(C5HiiNH)(C5HnNH2HO)02, that is, an isoamylamine salt of a 

 phenol, and this view was confirmed by the following observations : sodic 

 hydrate set free isoamylamine from it ; with hydrochloric acid a substance 

 was obtained having the formula CgCL(C5HnNH)H002, and melting 

 at 188°; argentic nitrate converted it into C6Clo(C5HiiNH)Ag002, 

 and we have also made the corresponding barium salt. That it was a 

 quinone was shown by its dark color and its conversion into a colorless 

 product by reduction. For the sake of comparison with this body we 

 made the dichlordiisoamylamidoquinone, C6Cl2(C5HiiNH)202, by the 

 action of isoamylamine on chloranil, it melted at 224° to 225°; and 

 also the isoamylamine salt of chloranilic acid, CyClo(OHH2NC5Hii)20o ; 

 both of which differed entirely iu properties from the product made from 

 the oxide. 



The oxide when treated with diisoamylamine gave a compound corre- 

 sponding to that from isoamylamine, C6Cl2(C5Hii)2N(C5Hii)2NHH002, 

 melting at 168° to 169°. With chloranil diisoamylamine gave 



C6Cl2((C5Hu)2N)202. 



In looking for actions analogous to those just described, we are obliged 

 to resort to the fat series, as no oxide similar to ours is known in the 

 aromatic series, the nearest approach to it being cineol according to the 

 formula ascribed to it by Briihl, in which, however, the oxygen spans 

 the benzol ring in the para position. In the fat series ethylene oxide 

 shows a structure similar to that of our oxide, as its atom of oxygen is 

 attached to two adjacent atoms of carbon ; and in its behavior with 

 various reagents we find a marked similarity to the reactions of our 

 oxide. Thus its conversion into glycol by the action of water corre- 

 sponds to the formation of chloranilic acid by sodic hydrate, and with 

 ammonia the ethylene oxide gives among other products an amino-alcohol, 

 HOCH2CH2NH2, analogous to the intermediate product which must 

 be formed by the action of isoamylamine on our oxide. On the other 

 hand we have not been able to find any case in which a fat oxide belong- 



