280 PROCEEDINGS OF THE AMERICAN ACADEMY 



XXL 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY 

 OF HARVARD COLLEGE. 



THE REACTIONS OF SODIC ALCOHOLATES WITH 

 TEIBROMTRIKITROBENZOL. * 



SECOND PAPER. 



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



Presented June 15, 1892. 



In our first paper on this subject we described some experiments 

 which led to the replacement of nitro groups in symmetrical tri- 

 bromtrinitrobenzol by ethoxy or methoxy radicals. These observa- 

 tions seemed to us of special interest because the three nitro groups 

 are in the meta position in this compound, and, so far as we were 

 aware, no case was known in which a nitro group in this position 

 to others had been removed from the benzol ring. In fact the so- 

 called rule of Laubenheimer stated that a nitro group is replaced 

 only when it is in the ortho position to another. Even with the 

 halogens cases where a radical in the meta position exercises a loos- 

 ening effect on another are very rare, the only one which occurs to 

 us being the conversion of symmetrical tribrombenzol into dibrom- 

 anisol by the action of sodic methylate.f 



Soon after the appearance of our paper C. A. Lobry de Bruyn 

 published an account t of some experiments with symmetrical trini- 

 trobeuzol and sodic methylate from which he obtained dinitroanisol, 

 thus again removing a nitro group in the meta position to others. 

 At the same time in an interesting discussion § of the replacement 

 of nitro groups in aromatic compounds he showed that Lauben- 

 heimer's rule must be abandoned, since para as well as ortho nitro 



* The work described in this paper formed part of a thesis presented to the 

 Faculty of Arts and Sciences of Harvard University for the degree of Doctor 

 of Philosophy, by W. H. Warren. 



t Blau, Monatsh. f. Ch., VII. 630. 



t Rec. Trav. Ch. des Pays-Bas, IX. 208. § Ibid., IX. 210. 



