166 Proceedings of the Royal Irish Academy. 



nitro radical is in the position 2'- since, if this were so, it is probable that the 

 4'- nitro compound melting at 283° 0. would be formed at the same time. It 

 is probable therefore that the compound is o-nitro-phenyl-2-naphthylamine, 

 unless the nitro group is contained in the second ring of the naphthalene 

 nucleus, which has not been considered here. 



The behaviour of nitrogen peroxide towards an alcoholic solution of the 

 stabiliser was next studied. From the facts mentioned below, it will be seen 

 that hydrolysis or alcoholysis of the aceto-naphthalide first takes place ; the 



nitration tli<*ii proc Is in two different ways, liefore attempting to trace 



the dual course of the nitration, it may be well to give the facts on which the 

 conclusions are based : — 



1. In alcoholic solution, the stabiliser, when treated with nitrogen 

 peroxide, slowly forms two trinitro compounds, one melting at 242° (J., and 

 the other at 179 I , 



2. When an alcoholic solution of the stabiliser is treated with colourless, 

 concentrated nitric acid il-l 1 * mols) and allowed to remain at the room 

 temperature for ten days, neither of the above compounds is formed. 



:;. In acetic acid solution, nitric acid (1-ii mols) has mi action on the 

 naph thai ide even after standing foi Borne months, but when amyl nitrite is 



added, the yellow trinitro c pound melting a i 242 C. and the orange 



■ me melting at IT l ■■ slowly formed. 



(. At ih liuary temperat are, in acetic acid solution, phenyl-2-naphthyl- 



nitrosamine is completely transformed by nitric acid il-ii mols into the 

 yellow trinitro compound melting ai ui'J C, mentioned above. 



5. In acetic acid solution in the presence of nitric acid (3-10 mols), 

 phenyl-.'-naphthvlaiiMne gives the orange trinitro compound melting at 

 I 



From u study of these results we can trace il [uence of the changes 



which the stabiliser undergoes in alcoholic solution, when the solution has 

 been previously: :ih nitrogen peroxide. The phenyl-aceto-naphthalide 



is first decomposed into the corresponding amine, which is partly nitrated 

 directly to bhi - .trinitro derivative melting al 17:' (.'.: another part, aboul 



three-fourths, of the amine is converted into phenyl-2-naphthylnitrosamine, 

 which in turn is transformed by the nitric acid into the yellow, trinitro 

 compound melting al -Ml' C. For the formation of the latter compound the 

 presence of nil 1 at some stage of the reaction seems to be essential. 



The yellow trinitro compound melting at 242° C. was found to be 

 2' - 4.'-trinitro-phenyl-2-naphthylnmine, having been prepared synthetically by 

 the combination of 1 chloro 2'4-dinitro-benzene with l-nitro-2-naphthylamine. 



