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No. 38. 



THE ACTION OF THE OXIDES AND THE OXYACIDS OP NITROGEN 

 ON DIPHENYLBTHYLENEETHER 



By HUGH RYAN, D.Sc, 



AND . 



TERENCE KENNY, M.Sc, 

 University College, Dublin. 



(Read December 18, 1923. Printed February 27, 1924.) 



Introduction. 

 It has been shown by one of lis in conjunction with J. Keane (No. 37) that 

 eth_yl-|-i-naphthylether interacts with the oxides and the oxyacids of nitrogen 

 with greater ease than phenylbenzylether. Each of these ethers contains two 

 nitratable rings — in the same radicle in the case of the naphthylether, and in 

 different radicles in that of phenylbenzjdether. 



Diphenylethyleneether, another ether which contains two nitratable rings, 

 resembles phenylbenzylether in so far as these rings are in different radicles. 

 On the other hand, as this substance approaches the aryl-alphyl ethers in 

 constitution, and is moreover a di-ether, it seemed of interest to examine its 

 behaviour towards nitrating agents, more especially under the conditions of 

 low temperatures and low concentrations employed in the previous investigations. 



The action of the oxides or the oxyacids of nitrogen on the ether, which 

 can be conveniently prepared from potassium phenolate and ethylene dibromide, 

 or ethylene dichloride, by the method of W. H. Perkin [Journ. Chem. Soc, 

 Ixix (1888), p. 165-166], has not been previously examined. 



Some of its nitro derivatives have, however, been already obtained by the 

 combination of nitrophenols with ethylene dihalides. Thus A. Weddige [Journ. 

 f. pr. Ch. (2), xxi (1880), p. 127] prcpai'ed 2-8-dinitrocliphenylethyleneether'^ and 

 4-10-dinitrodiphenylethyleneether from ethylene dibromide and the potassium 

 derivatives of the corresponding nitrophenols. He also obtained a substance 

 [Journ. f. pr. Ch. (2), xxiv (1881), pp. 241-256], melting at 86° C, which he 

 termed 2-nitrodiphenylethyleneether, from phenylbromethylether and a body 

 which he assumed to be 2-nitrophenol. E. Wagner [Journ. f. pr. Ch. (2), xxvii 

 (1883), p. 201] prepared 3-9-dinitrodiphenylethyleneether by a similar reaction. 



Before attempting to isolate the products of the interaction of the oxides 

 and the oxyacids of nitrogen with the ether, we deemed it advisable to prepare 

 the simpler nitro derivatives of the latter from ethylene dibromide, or dichloride, 

 and the potassium derivatives of the corresponding nitrophenols, so as to 

 determine the properties of the pure substances, with a view to facilitating their 

 isolation from the nitration mixtures. 



By the action of potassium p-nitrophenolate on phenylbromethylether we got 

 a compound (4-nitrodiphenylethyleneether) which corresponded in melting- 



^ The nomenclature adopted in this communication is based on the following structural 

 formula for diphenylethyleneether : — 



<4 lN_o_CH2— CH2— 0— /? 10> 



\ 6 6 / \ 12 11 / 



SOIENT, PROC, K.D.S., VOL. XVII, NO. 88. 3 M 



