288 REPORTS ON THE STATE OF SCIENCE. 
yield of triphenylhydrazine. Possibly azobenzene is formed as an intei’. 
mediate product, and then interacts thus :— 
C,H, C,H, 
C,H, N:N. Css Gat Mebee pan NC 
CH \MgBr 
An alternative explanation is suggested as more probable. Phenyl- 
hydroxylamine is partially converted into diphenylamine, which then 
condenses with phenylhydroxylamine : 
(C,H,),NH + OH . NHC,H, =(C,H,).N / NHC,H, + H,0 
It might be noted here that magnesium organic compounds sometimes 
exhibit a reducing action, Franzen and Deibel,! for example, show that 
hydrazobenzene may ‘e obtained in good yield from azobenzene and mag- 
nesium ethyl bromide. 
C,H; .N Jods C,H; .N . MgBr 
| + aMeX. s +C,4,, 
6H; .N Br C,H, .N . MgBr 
C,H, .N .MgBr C,H, .NH 
| +2H,0= x + 2MgBr(OH) 
C,H, .N.MgBr C,H, . NH 
The action of the Grignard reagent on nitro-compounds has not been very 
thoroughly investigated. Moureu? obtained diethylhydroxylamine by 
the action of magnesium ethyl iodide on nitroethane and amylnitrite 
respectively. One of the products resulting from the action of magne- 
sium ethyl iodide on nitrobenzene is ethyl aniline.* 
A method of obtaining secondary amines from alkylidene bases is de- 
scribed by Busch ;‘ thus C-methyl benzylaniline is obtained from magne- 
sium methyl iodide and benzylidene aniline : 
C,H;.N: CH, C,a,+ MgCH,1=C,H, . N——CH . C,H, 
as 
MglI CH, 
C,H, . N——CH . C,H, + H,0 =0,H,NH . CH(CH,) . C,H, + MglOH 
| 
MgI CH, 
The action on oximes has been studied by Buscli and Hobein,’ and 
takes place in accordance with the scheme 
R R oH 
R.CH:N.OH+2R/MgX= SCH.NC 4+Me% 
RY \Mex NX 
R RY R oH 
Seu NC. 48,0= SCH. NHR’ + Mef 
Rv \ Mex RY he 
According to F. and L. Sachs,° tertiary amines combine with mag- 
nesium organic compounds to form compounds which are insoluble in 
1 Ber., 1905, 38, 2716. 2 Compt. rend., 1901, 132, 837. 
* Oddo, Atti R. Accad. Lineei, 1904 [v], 13, II. 220. 
* Ber., 1904, 87, 2691. Compare Busch and Rinck, idid., 1905, 38, 1761., 
5 Tbid., 1907, 40, 2096. 
; = Ibid., 1904, 87, 3088. Compare Oddo, Atti R, Accad. Lincei, 1904 [v], 18, 
. 100. 
