JACKSON AND GAZZOLO. — NITRO COMPOUNDS. 267 



Conversely this benzyl compound is converted into the corresponding 

 methyl compound if boiled with methyl alcohol. In the same way * the 

 methyl is converted into the ethyl compound by crystallization from 

 common alcohol. f 



There are three possible ways in which these compounds can be 

 formed : — First, the addition of the sodic methylate (or other alkaline 

 substance) may take place upon the carbon atoms of the benzol ring. 

 Second^ it may take place on the nitro group alone. Third, it may take 

 place partly on the nitro group and partly on the carbon of the benzol 

 riucr. 



The first method of addition, that on the carbon alone, seems to us 

 much less probable than the second or third, in which a nitro group takes 

 part, especially since the work of Nef and others has shown that the 

 sodium is attached to the nitro group in the sodium salt of nitromethane. 

 As we have succeeded in finding no analogous case in which an alkaline 

 substance is added to carbon atoms with the formation of a strongly col- 

 ored product, we think that this first hypothesis is not worthy of a 

 detailed discussion. 



Turning to the formulas in which the nitro group is affected, we have 

 the second method of addition, in which the sodic methylate is attached 

 to the nitro group only ; this would give rise to a structure such as the 

 following : | — 



I. 



OCH3 



C6H20CH3(NO.,)o— N 



ll\ 



O ONa; 



while the third hypothesis, according to which both the nitro group 

 and the carbon of the benzol ring take part in the addition, would be 



* These Proceedings, XXXIII. 177. 



t Some experiments of less importance may be mentioned here, witli the 

 remark that they are not incompatible with tlie formula adopted later as 

 giving the best explanation of the observed facts. Bromine decomposes 

 CsH3(NO.,)3[CHNa(COOC.,H5)2]3, giving trinitrobenzol as one of the prod- 

 ucts of the reaction. No salts with other basic radicals could be obtained 

 from C,.H.,(NOo)30CH3XaOCH3. No sodic iodide was formed by heating 

 CsH3(N02)3[CHNa(COOCoH5)._,]3 with ethyl iodide to 140°. On tlie other hand, 

 it looked as if benzoyl chloride acted on these bodies, but the end of the college 

 year prevented us from studying this reaction. 



t This is analogous to that given by Hantzsch and Rinckenberger, Ber. d. chem. 

 Ges., XXXII. 628, for their dinitroethanester acid. 



