Ryan & O'Donovan — Action of Oxides, Sfc, on Pheni/l-benzyliir ethane. 137 



Summary. 



1. Like other teiiiaiily constituted aromatic urethaiies, phenyl-lenzylurethaue 

 is difficult to nitrate. The benzyl radical can, however, be nitrated, as well as the 

 phenyl radical, without the decomposition of the urethane. 



2. Nitrogen peroxide converted the urethane into 4-nitro-phenyl-benzyl- 

 nrethane, melting at 70° C, and a trinitro-phenyl-benzylurethane melting at 110° C. 

 A small amount of oxalic acid was also formed. 



3. At low temperatures and at low concentrations nitric acid acted on the 

 urethane, forming again 4-nitro-phenyl-benzylurethane and oxalic acid. 



At higher concentrations of the nitrating acid the urethane was converted into 

 the trinitro derivative, melting at 110^ C. 



4. When the temperature was more or less high and the concentrations were also 

 higli, a tetranitro-phenyl-beiizylurethane, melting at 126^ C, and a crystalline 

 substance, melting at 274° C. (probably a pentanitro-phenyl-benzylurethane), were 

 formed. 



Secondary reactions also occurred. These were attended by the formation of 

 4-nitro-benzoic acid, 2'1-dinitro-phenylurethane, and pentanitro-phenyl-benzyl- 

 urethane. 



In conclusion we wish to state that the above research was undertaken at the 

 request of the Eesearch Section of Nobel's Explosives Company, to whom we are 

 indebted for a grant in aid of the investigation. 



