132 Scientific Proceedings^ Royal Dublin Society. 



of 4-nitro-phenyl-benzylurethane/ since on hydrolysis it yielded 4-nitro-phenyl- 

 benzylamine. 



In our experiments nitrogen peroxide converted the urethane into an oily 

 mixture, from which 4-nitro-phenyl-benzylurethane, melting at 70° C, a trinitro- 

 phenyl-benzylurethane. melting at 110° C, and oxalic acid were isolated. 



The urethane was converted by nitric acid at low temperatures or low con- 

 centrations into oxalic acid and 4-nitro-phenyl-benzylurethane, the constitution of 

 the latter substance being established by its conversion on hydrolysis into 4-nitro- 

 phenyl-benzylamine. With a higher concentration of the acid we obtained a trinitro- 

 phenyl-benzylnretbane melting at 110° C, which, from its formation from 4-nitro- 

 phenyl-benzylurethane and from analogy, is probably either 2-4'10 or 4'8-10- 

 triuitro-phenyl-benzylurethane. Further nitration of this compound, or the action 

 of a mixture of sulphuric and nitric acids on the original urethane at a low 

 temperature, resulted in the formation of a tetranitro compound, probably 2-4'S-lO- 

 tetranitro-phenyl-benzylurethane melting at 126° C. 



When the temperature at which " mixed acid " was allowed to act on the 

 urethane was not kept continuously low, a yellow viscid mass was obtained, from 

 which we isolated a crystalline substance melting at 274" C, which was probably 

 2'4-6'810-peutanitro-phenyl-benzylamine, and a crystalline substance melting at 

 238° C, the properties of which indicated its identity with 4-nitro-benzoic acid, 

 and in addition a much reduced yield of the tetranitro-phenyl-benzylurethane 

 previously mentioned. 



When the urethane was nitrated by heating with " mixed acids " for several 

 days on the water-bath, with addition of nitric acid from time to time, and by 

 subsequent treatment with potash, a fair yield of 2'4-dinitro-phenylurethane was 

 obtained, and also 4-nitro-benzoic acid and a compound melting at 264° C, which 

 was probably either a triniti'o-phenyl-benzylamine or pentanitro-phenyl-benzyl- 

 urethane, were obtained. 



Owing to the facts that no dinitro derivatives were isolated, and that the 

 positive evidence available is insufficient, the course of the reactions is somewhat 

 difficult to trace. The urethane yields first the 4-nitro-phenyl-benzylurethane, and 

 then, probably through dinitro derivatives, a trinitro-phenyl-benzylurethane, only 

 the 4-position of which is known to be occupied by a nitro group. However, since 

 further nitration is attended by the simultaneous formation of 2 4-dinitro-phenyI- 

 urethane and 4-nitro-benzoic acid (tlie latter indicating a nitro group in the 

 10-position), it is very probable that the constitution of this trinitro compound is 

 2'4'10 -trinitro-phenyl-benzylurethane. The next stage in the reaction is the 

 formation of a tetranitro derivative and the probable formation of a pentanitro- 

 phenyl-benzylurethane, with simultaneous decomposition of the urethane group, 

 yielding pentanitro-phenyl-benzylamine. 



' The nomenclature adopted in this communication is based on the following formula : — 



/Z 2\ R /8 9\ 



(i l\ N— CH2 A lo\ 



^ ,5 t, ^ \ 12 11 / 



where R is either H or OOOC2H5. 



