76 PROCEEDINGS OF THE AMERICAN ACADEMY. 



After the coustitutiou of the 1. 3.4. 6 dibromdinitrobenzol had been 

 determined, we studied the action of sodic ethylate upon it, in the hope 

 of encountering the replacement of bromine by hydrogen uuder the action 

 of this reagent, which has been studied for some years in this Labora- 

 tory. But no such behavior was observed ; the action ran iu the normal 

 way, resulting in the formation of the diuitroresorcine diethylether melt- 

 ing at 133", discovered by Warren and one of us,* and proved to have 

 the symmetrica] structure by Koch and one of us t ; so that this observa- 

 tion confirms the determination of the constitution of this body by the 

 action with aniline. 



Sodic phenylate converted the dibromdinitrobenzol into diphenoxydi- 

 nitrobenzol, which melts at 129°. The action of sodic malonic ester was 

 tried on this compound to determine whether the phenoxy groups could 

 be replaced by the malonic ester radical CH(COOC2H5)2 ; as it has 

 been found t that the best way to make dichlordimalonicesterquinone 

 CgCL[CII(COOC2H5)2].202 is by treating dichlordiphenoxyquinone with 

 sodic malonic ester, and we wished to see whether the nitro groups 

 would produce the same effect as the oxygen atoms of the quinone in 

 promoting the replacement of the phenoxy groups by malonic ester 

 radicals. We found that phenol was eliminated when the diphenoxy- 

 diuitrobenzol was treated with sodic malonic ester, and from the very 

 unmanageable product a sodium salt was obtained which contained an 

 amount of sodium corresponding to CeH.,OC6H5CNa(COOC2H5)2(N02)2 ; 

 so that we feel justified in assuming that the reaction has consisted in 

 the replacement of the phenoxy by tlie malonic ester group. 



The dibromdinitrobenzol, when reduced with zinc dust and acetic acid, 

 gave a dibrommetaphenylene diamine, wliich was identical with that 

 melting at 135° obtained by the action of bromine on metaphenylene 

 diacetamid. § It follows from our preparation of this base that it has 

 the constitution Brg 1. 3. (NH2)2 4. G. 



In all this work we have been careful not to approach too near to the 

 field reserved by Nietzki and Schedler in their paper on dichlordinitro- 

 benzol. 



* These Proceedings, XXV. 170. 



t Ibid. XXXIV. 134. 



t Jackson and Grindley, Ibid. XXX 425. 



§ Jackson and Calvert, Ibid. XXXI. 150. 



