256 PROCEEDINGS OF THE AMERICAN ACADEMY 



XXI. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ON THE ACTION OF SODIUM MALONIC ESTER UPON 

 TRIBROMTRINITROBENZOL. 



By C. Loring Jackson and George Dunning Moore. 



Presented May 28, 1889. 



In a previous paper * one of us with J. F. Wing described the prepa- 

 ration of tribromtrinitrohenzol, and announced that its action with 

 sodium malonic ester would be studied. This work promised to be 

 of especial interest, because we hoped that each of the bromine atoms 

 would be replaced by the radical CH(COOC 2 EL) 2 , and that by the 

 reduction of the substance thus formed a compound might be obtained 

 consisting of three pyrrol molecules united to form a central benzol 

 ring, a sort of triple indol. Our first experiments, however, showed 

 that the reaction did not run in the way we had expected, but instead 

 of the removal of all three of the bromine atoms only two were re- 

 placed, one by the radical CH(COOC 2 H 5 ) 2 , the other by hydrogen 

 giving a product with the following formula, 



C 6 HBr(N0 2 ) 3 CH(COOC 2 H 5 ) 2 , 



that is, bromtrinitropheuylmalonic ester. After we had established 

 the composition of this substance, we decided that it was unwise to 

 undertake a complete study of this trinitro compound, which can be 

 obtained only with a very considerable outlay of time and material, 

 when the corresponding dinitro compound can be made much more 

 easily, and resembles it closely in most respects. "We have accord- 

 ingly confined our work principally to those properties of the trinitro 

 componnd in which we have observed marked differences from the 

 corresponding ones of the dinitro body, and for a fuller discussion of 

 those properties which the two substances have in common would 



* These Proceeding, xxiii. 138. 



