298 Scientific Proceedings, Roi/al Dublin Society. 



Concentrated nitric acid acted readily on the etlier forming the 1-6- and 

 1-8-dinitro derivatives; and when the temperature was allowed to rise to 

 50° C, a trinitro compound was obtained not only from the ether itself, but 

 also from both its 1-6- and IS-dinitro derivatives. This body is, therefore, 

 l-6-8-trinitroethyl-/3-naphthylether. It was converted by alcoholic ammonia 

 into l-6-8-trinitroethyl-f:J-naphthylamine, which melted with decomposition at 

 300° C. 



An attempt to prepare higher nitrated derivatives of the trinitro body led 

 to the formation of decomposition products. 



The results obtained by us are shown in the following diagram : — 



Etbyl-yS-naphthyleiher 

 ■(M.P. 37° C.) 



\!/ 



„ l-Nitroethyl-S-naplithvlelher 



(M.P. 104-105°C.") 



si/ s!/ 



l-G-Dinitroethyl-0-nai>hthyletlier l-8-Diniiioeihvl-j3-iiaphthylether 



(M.P. i44-145''C.)' (M.P. 216-2 17° C.) 



I . I 



1-6-S-Triiiitroethyl-S-nfiphthyletliei' 

 (M.P.'189°C.) 



l'6-8-Trinitio-;8-iiaiihthylaniine 

 (M.P. 300° C.) 



Experimental. 



1. Action of Nitrogen Peroxide on Ethyl -f3-napMJiylether. 



(a) In the Absence of Solvents. — A shallow glass vessel containing 1-5 g. 

 of ethyl -/3-naphthylether was allowed to remain in an enclosed space filled 

 with nitrogen peroxide vapour. The ether first turned brown, then became 

 liquid, and finally changed to an orange-red oily solid. After three days the 

 solid was washed with ether. The ethereal washings contained a trace of red 

 oily matter, soluble in alkali, and a solid, which crystallised from alcohol in 

 colourless needles, melting at 144-145° C, and gave on analysis the following 

 results : — 



01946 g. substance gave 17-8 c.c. moist nitrogen at 13° C. and 760 m.m. 



corresponding to N 10- 8 

 CioHioO^Nj requires N 10-7. 



. The substance was, therefore, a dinitro derivative of ethyl -|3-naphthylether. 

 When heated in a sealed tube with alcoholic ammonia, it was converted into 

 1-6-dinitro-^-naphthylamine, which separated as golden yellow tabular prisms, 

 melting with decomposition at 247° C. The substance, which melted at 144- 

 145° C, was, therefore, 1-6-dinitroethyl -/3-naphthylether. It is very soluble in 

 warm organic solvents, moderately soluble in cold chloroform or acetic acid, 

 and only slightly soluble in alcohol or benzene. 



The residue left on washing the nitration product with ether was recrystallised 

 from boiling benzene; Colourless rectangular prisms, melting at 216-217° C, 



