Ryan and O'Kiohdan — On a-, /3-, and y-Trinitrotolvenes. 193 



The action of amines on the three t rinit ti >t,i iliunieM also proceeds somewhat 

 differently in the three cases. One interesting fact is, that an additive com- 

 pound of the y-isomer with p-toluidine has been isolated. Hepp. (loc. cit.) 

 stated that neither |3- nor -y-trinitrotoluene formed simple additive compounds 

 with primary amines. It is probable that additive compounds are also 

 formed by /3-trinitrotoluene ; but, if so, they are very unstable. The action 

 of ammonia and amines on the substances seems to show that the /8-isomer 

 yields a toluidine or diphenylamine derivative as readily as the y-eompound, 

 whereas Hepp's statements (loc. cit.) would lead one to think that the latter 

 was in this respect much more reactive than the former. 



The reactions of the trinitrotoluenes with aldehydes show clearly a differ- 

 ence in the reactivity of the CH 3 group in these substances, the o-isomer being 

 the only one from which stilbene derivatives were obtained. 



Attention may be drawn to the fact, mentioned above, that a sample of 

 crude -y-trinitrotoluene was found to contain a dark, amorphous substance, 

 which explodes on heating. In view of the facts mentioned in the introduc- 

 tion to this paper, this may be of considerable interest. 



In conclusion, we wish to thank Nobel's Explosives Company for the 

 materials employed in our experiments; and Mr. Eintoul, the Manager of 

 the Research Section of that Company, at whose suggestion the investigation 

 was undertaken. 



We also desire to thank the Advisory Council for Scientific and Industrial 

 Research for a grant which enabled us to carry out the work. 



