CONTRIBUTIONS FROM THE CHEMICAL LABORATORY 

 OF HARVARD COLLEGE. 



ON CERTAIN COLORED SUBSTANCES DERIVED FROM 

 NITRO COMPOUNDS. — THIRD PAPER. 



By C. Loring Jackson and F. H. Gazzolo. 



Presented December 13, 1899. Received December 30, 1899. 



The colored substances formed by the action of sodic alcoholates and 

 certain nitro compounds have been studied by Victor Meyer,* Lobry de 

 Bruyn,f and in this Laboratory, t but as yet no satisfactory constitutional 

 formula has been assigned to them. 



In continuing this investigation, we tried first to replace the sodic 

 alcoholates by other similar reagents, and succeeded in obtaining colored 

 products from trinitranisol or trinitrobenzol by the action of sodic malo- 

 nic ester, sodic acetacetic ester, sodic phenvlate, the sodium compound of 

 benzylcyanide, and perhaps the sodium compound of phloroglucine, al- 

 though in this last case the action was not well marked. As it has been 

 shown already that similar compounds are formed with various sodic 

 alcoholates, § and even with sodic hydrate, || it appears that this behavior 

 with nitro compounds is a very general reaction of alkaline substances. 



Of these new colored products only those with sodic malonic ester or 

 sodic acetacetic ester were stable enough to be prepared for analysis, but 

 they were unusually stable for bodies of this class. All four of the sub- 

 stances formed from trinitranisol or trinitrobenzol and these two sodium 

 esters were analyzed, and were proved to consist of three molecules of 

 the sodium ester combined with one of the trinitro compound ; for in- 

 stance, the malonic ester trinitrobenzol compound has this formula, 



* Ber. d. chem. Ges., XXVII. 3153; XXIX. 848. 



t Rec. Trav. Chim. Pays-Bas, XIV. 89, 150; XV. 848. 



t Jackson and Ittner, Am. Chem. Journ., XIX. 199, where a historical account 

 of the previous work is given ; Jackson and Boos, These Proceedings, XXXIII. 

 173. 



§ These Proceedings, XXXIII. 173. 



II Hepp, Ann. Chem. (Liebig), CCXV. 359. 



