192 Proceedings of the Royal Irish Academy. 



which imply that while y-trinitrotoluene reacts with alcoholic ammonia on 

 the cold, the /3-isomer reacts only when treated with alcoholic ammonia in a 

 sealed tube. 



/3-trinitrotoluene reacts with aqueous ammonia, yielding a small quantity 

 of dinitrotoluidine,and a similar reaction takes place in the case of the y-isomer. 



o-triuitrotoluene forms an additive compound with />-tohudine. This 

 compound has been previously described by other workers. (Jackson and 



ike, Proa Chem. Soc., 10oo\ p. 83.) 



(3-trinitrotoluene reacts very readily with both aniline and p-toluidine in 

 alcholic solution, yielding substituted diphenylamine derivatives. 



y-trinitrotoluene with p-toluidine forms an additive compound, which is 

 readily transformed into a substituted diphenylamine derivative. TlmsHepp's 

 statement that y-trinitrotoluene does not form simple additive compounds 

 with amines is incorrect. 



3. o-trinitrotoluene reacts readily with piperonal, anisaldebyde, and 

 benzaldchyde on the water-bath, in the presence of piperdine forming stilbene 

 derivatives, Neither the/3- nor they-isomcr underwent such a reaction even 

 at 130 I 



4. All three isomeric trinitrotoluenes form additive compounds with 

 phenantln 



The results obtained show thai the four substances examined all react 

 differently with alkalies. There are, howevei some points of agreement. In 



each case a ; eduction takes place, as shown by il volution of 



ammonia; but it is nol possible ly how this reduction takes 



place. The reduction probably in all cases proceeds to the formation of an 

 amine, the Ml. group being then i IB with evolution of ammonia. 



In all four cases the reaction is by no means so Bimple as this might imply. 

 Phenolii implex nature are apparently formed in considerable 



quantities, their formation probably following a reaction such as is indicated 



here. 



Simultaneously with this reduction there is in the ease of o-trinitrotoluene 

 a process of oxidation with formation of hexanitrodibenzyl. This is the only 

 case in which we have definite proof of a process of oxidation : but it may be 

 pointed out that non-phenolic substances were obtained from s-trinitrobenzene 

 and y-trinitrotoluene, which may possibly be derived from these .substances by 

 such a process. Symmetrical trinitrobenzene is unique in thai it yields con- 

 siderable quantities of a tetranitro-azoxy compound. 



In most cases dark-coloured substances insoluble in alkali were formed, 

 and these exploded on being heated. 



