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PROCEEDINGS OF THE AMERICAN ACADEMY. 



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

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

 ing auilidouaphthoquiuoneanil, CioH50(C6H5NH) (CeHgN), which is 

 undoubtedly a derivative of alpha-uaphthoquinone. Zincke * also has 

 obtained recently from the azimidodichlororthoquinone by warming it 

 with aniline an azimidoanilidomonochloroxyparaquinone, and similar 

 cases of conversion of orthoquinones into derivatives of para- 

 quinones are not rare. We are so strongly of the opinion, therefore, 

 that our dianilidoquinoneauil is a para body with the constitution 

 0, 1. CeHgN, 4. (CeHsNH)^, 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- 

 quiaone by the following series of transformations, which are modelled 

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

 of beta-naphthoquinone : — 



II. 



III. 



IV. 



aH,NH 



o 







C«H.,NH 



-'6 "5 



NHCeHg 



OH 



CeHsNH 



NCfiHs 



The replacement of the two hydrogen atoms of the orthoquinone by 

 the anilido groups to form II. takes place under the oxidizing influence 

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

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

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

 of aniline. 



Upon treating the solution of orthoquinone with orthophenylene- 

 diamine no phenaziue was formed, but the reaction seemed to consist 

 only in the oxidation of the diamine. 



We have also devoted some attention to the study 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), CCCXI. 276. 

 t Ber. d. chem. Ges., XIV. 16G4. 



