164 PROCEEDINGS OF THE AMERICAN ACADEMY 



X. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 

 HARVARD COLLEGE. 



THE REACTIONS OF SODIC ALCOHOLATES WITH 

 TRIBROMDINITROBENZOL AND TRIBROM- 

 TRINITROBENZOL. 



By C. Loring Jackson and W. H. Warren. 



Presented May 27, 1890. 



We were induced to take up this piece of work — although at first 

 sight it might seem to promise little of interest, either in the new 

 compounds formed or in the nature of the reaction — by some experi- 

 ments in a previous research which apparently indicated that one of 

 the atoms of bromine in tribromdinitrobenzol would be replaced by 

 hydrogen under the influence of sodic ethylate. If this was the 

 case, the work would supply additional material on which to found 

 an explanation of the substitution of bromine by hydrogen in the 

 formation of bromdinitrophenylmalonic ester and allied compounds, 

 described in several previous papers* from this Laboratory. Not 

 only has the promise of these experiments been fulfilled, but the 

 work has surpassed in interest all that we expected of it, as it has 

 shown that sodic alcoholates (under which name we class phenolates 

 also) act on tribromdinitrobenzol and tribromtrinitrobenzol in four 

 different ways : — 



First. A simple replacement of each atom of bromine by the radi- 

 cal of the alcoholate. This we have observed only in a single case, the 

 action of sodic phenolate on tribromtrinitrobenzol giving trinitrophlo- 

 roglucine triplienylether, Cg(NO.,)3(OCgH5)3, melting point 175''. 



Second. The replacement of two atoms of bromine by two of the 

 radical of the alcoholate, the third atom of bromine remaining unal- 

 tered. Under this head come the actions of sodic ethylate in the cold, 



* These Proceedings, xxiv. 1, 256, 271, 288, 30G (1888-89). 



