202 



PROCEEDING OF THE AMERICAN ACADEMY. 



able that a derivative of orthoqninone would be so stable as this; and 

 the beta-naphthoquinone forma with aniline and alcohol a correspond- 

 ing anilidonaphthoquinoneanil, I : H 6 0(C H 6 NH)(C II.-X). which is 

 andoubtedly a derivative of alpha-naphthoquinone. Zincke* also has 

 obtained recently from the azimidodichlororthoquinone by wanning it 

 with aniline an azimidoanilidomonochloroxyparaquinone, and similar 

 ■ if conversion of orthoquinones into derivatives of para- 

 quinones are nut rare. We are so strongly of the opinion, therefore, 

 that our dianilidoquinoneanil i- a para body with the constitution 

 i ). 1. ( II X. I. | ( . II XII i ,,2.5, that we have not thought it worth 

 while to submit the question to an experimental investigation, which 

 would of necessity occupy much time. Assuming that the constitu- 

 tion given above is correct, the body would be formed from the ortho- 

 quiuone by the following series of transformations, which are modelled 

 after those worked out by C. Liebermann f for the corresponding case 

 of beta-naphthoquinone : — 



I. 



II. 



III. 



IV, 



C 6 H 6 NH 



O 



C .II-XII 



MK' II, 



C II 6 NH 



NC 6 H 6 



O 



NIK .11 



6"5 



N'MI;, 



The replacement of the two hydrogen atoms of the orthoquiuone by 

 the anilido groups to form II. take- place under the oxidizing influence 

 of another portion of the orthoqninone, which takes up hydrogen to 

 form pyrocatechine (always formed in our process) ; II. then passes by 

 isomerization into III., which i- converted into IV. by the further action 



of anil': 



Upon treating the solution of orthoqninone with orthophony lene- 

 diamine no phenazine was formed, bul the reaction seemed to coi 



Only in the oxidation of the diamine. 



\\ ■ bave also devoted some attention t" the Btudy of the tetrabrom- 

 orthoquinone, and have obtained from it two derivatives. The first of 

 these was prepared by treating tetrabromorthoquinone with tetrabrom- 

 pyrocatechine dissolved in acetic acid and water; it was a beautiful red 



• Ann chem. (Liebig), CCCX] 276. 

 Bi r. d. chem. <■■ i., XIV. II I 



