TRANSACTIONS OF SECTION B. 643 



-N-H 



atoms are linked together, viz., C.H, \ . If Kekule's formula is tlie right 



-N = N 



one, the monosubstituted ortho-diamines CvH, " -II, should also yield azimiJo 



-Nil, 

 derivatives on heing acted upon with nitrous acid, while if Griess's formula were 

 exact, the formation of azimido derivatives from monosubstituted ortho-diamiues is 

 only explicablebv admitting a rather complicated molecular transposition. We there- 



"V ~* P TTo 



fore prepared the mono-ethyle-ortho-toluylene-diamine, CJi„ " -tt- 1, and 



" -NH., 2 



- CH,; 4 



acted upon it with nitrous acid. By this means we obtained an azimido-compound, 

 crvstallisiug from alcohol in small white needles of the melting-point 147°, in- 

 soluble in alkaline solutions, whilst the ordinary azimido-toluene is soluble, and 



-N-Na 

 even forms a crystallised sodic compound Cgllj (CII3) \ . The same ethyle- 



-N=N 

 azimido-toluene was obtained by the action of ethylic iodide on the sodic azimido- 

 toluene, and this body has therefore evidently an analogous constitution, 



-NH 

 0.113(0113) \ . In our opinion the action of nitrous acid on the three series 



— N = N 

 of diamines is in the first stage the same. 

 Paradiamines yield diazoic salts — 



,, p„ -TsHJICl „.-P, TTO^PW -^^ = N-C1 

 1 4. C,H, _ ^ jj- jj^.j + HN 0, = 11,0 + C, H, _ ^-h,HC1 



and under the influence cf a large excess of nitrous acid, even bidiazoic salts, 



CgH^ ^' ^ pi. MetEyiiamines also yield diazoic salts, but these reach upon 



another molecule of diamine, and form a Manchester brown — 



, „ p „ N = N - CI p „ NH, _ (. „ - N = N - C«H3(NH,),(IIC1) 



In the case of ortho-diamines the diazoic group reacts on the amido group of 

 the same molecule, and yields a kind of internal anhydride, the azimido body. 



A- x- PI -N = N 



12. C,H, ~ ^-rr ~ ^ = HCl + C,H, / 



^-^^i. -N-H 



The azimido-compounds in their constitution have some analogy with thediazo- 



— C II 



amido-compounds, CgH^- X = N— N_tt' ^ but are distinguished from the latter 



by their stability. 



5. On the Constitution of the Mixed Diazoamido-compounds} 

 By Drs. Noelting and Binder. 



Griess has shown several years ago that by the action of a diazo-compound 

 Ii_X = N — CI on an amine R'NH,, one obtains the same diazoamido-compound as 

 by the action of K' — N=N — CI on II — NH,. It is not possible to decide from 

 Griess's experiments whether the resulting compound has the constitution 



Ii_X=N — N TT or R' — N = X — X_TT. Griess has proposed a (CgH^)" = 



N =X =N = (HgH^)", which seems to us to be not probable. 



I I I 

 H H II 



' These two papers are published in the Bcriclde dcr Dentschen Cliemischcn 

 Gcsclhchaft, and in the Bulletin de la Societe Iiuhtdrielle de Mullwvse. 



T T 2 



