644 KEPORT — 1887. 



We have undertaken a new study of this subject, and have especially taken into 

 consideration the product from diabenzenecbloride and paratoluidine, and from 

 diazoparatolyl-cbloride and aniline. The properties of these two compounds which, 

 as Griess has proved before us, are in every respect identical, do not allow us to give 

 to them a definite formula. In some reactions their behaviour corresponds to the 



formula of diazobenzene-paratoluide, (C^ILN = X) —N_j-, TT ; in some others to 



the formula of diazoparatolyl-aniliJe, (C.Il7X = X)— X~(' tt i iu others, finally, 



the most numerous ones, the compound has the properties of a mixture of these 

 two derivatives. AVe therefore prefer to use for the compound the formula 



f'^TT^ f ^3^^' '"''^'ch includes the two possibilities. Accordiug to our opinion we 



have here a new case of so-called tautomerism. 



If in the amines II — NH^ and K' — XII, one atom of H be substituted by an 

 alkyle group, the diazoamido-compounds obtained by the action of 11 — X = X" — CI 

 andR' — X=X — CI are no longer identical but different (isomeric). The above 

 experiments were performed in the year 1S84, but had not been published in 

 cxtenso, because they did not allow us to decide the question of the constitution of 

 the mixed diazoamido-compounds. If we now allow ourselves to present them to 

 this Section, the reason is that other chemists, especially Mr. ^Meldola, devote them- 

 selves to similar researches, and whilst we hope that our observations may contri- 

 bute in some way to the resolution of this interesting question, at the same time 

 we declare that it is not our intention to work ftirther on this subject. 



By the action of C«H,X = X-C1 on C,H,XII„ and of C,iLX = N-01 on 

 C TT 1 ' ' ' 



CgHjNHj, one obtains p^-rr^ V X'jII, yellow needles of the melting point 85°, soluble 



in the usual solvents, except water. 



The following experiments were always made with specimens obtained by the 

 two different methods. 



(rt) Action of nascent H — produces C^IIXn.,, C,n.XII XII,,, and simulta- 

 neously C,H,XIL, C.HjXH XII,. 



(h) Action of bromine — produces C^H^X = X — Br and C,iII.,Br.jXn.,. 



(e) Transposition with aniline — produces Cgll.X = N — C^II^XII., and C,H,XH,3. 



{(I) Transposition with dimethylaniline — produces C^HjX =X — Cgll^X^CHg), 

 and CgH-,XII,. 



(e) Transposition with phenol in excess — produces C^H-X =X — Cj;Hj(OH) and 

 C7H,XIIo. Ilenmann and Oeconomides with the theoretical amount of phenol 

 obtained Cgll.X = X - C,iI,(OII), C JLX = X - C.II.OII, 0-ILXH., and C,JI,XH.,. 



(/) Splitting up witli dilute II.SO^'— prod uces CJI.OIl'. C',II-Xn.„ and simul- 

 taneously C,II;On, C,-,II,XII,,. 



{(f) Ethylation and decomposition with dilute II^SOj. The product obtained 

 by acting in alcoholic solution with sodium and ethvlic iodide is a vellow oil ; with 



.— c ii 



dilute sulphuric acid it splits up into C.-II-^OII and C-IT-X'_ j^- ■', and simulta- 

 neously C,H,OH and C,H,X~ Jj-"\ 



II. Action of C,H,X=X-ClonC,irX~Jj'^^', and of CJI,X = X-C1 on 



C^H^N ~TT '" ; p^TT* r^^sCCjH^)- Tlie first is a yellow oil ; the second forms red 



crystals m. p. 38°-30°. 



(a) Action of the nascent H. 



The first gave C,H,XH.XII, and C^II.X ~ ^j^^^-' ; the second C.IIjXII.XH^ 



-C TT 

 and C-H,X_jj^^^5. 



ih) Splitting up with dilute 11,80^. 



