132 Journal of the Asiatic Society of Bengal. [March, 1913. 
intermediate product. Chlorine in combination with phos- 
orus, arsenic, or boron does not decompose the base but 
forms definite compounds (Michaelis, Oster, Annalen, 1892, 
270, 123), whereas stannic chloride causes complete rupture of 
it. Again, the decomposition of the diazonium salt in the 
presence of a hydroxyl group is much influenced by the radical 
with which it is combined. Phenol and nitrogen are forme 
by its decomposition in aqueous solution :— 
C,H,N,Cl + H,O=C,H,OH + N, + HCl. 
n alcoholic solution the products are not quite similar, 
the alcohol causing partial reduction of benzene diazonium — 
salt, being itself oxidized to aldehyde (Griess, Annalen, 1866, 
137,69; 18:3, 217, 189: Ber... 1876, 9, 899). 
(1) C,H,N: NCl+C,H,OH =C,H,OH + N, + C,H,Cl. 
(2) C,H.N: NCl + CH,CH,OH=C,H, +N, + HCl + CH,.CHO. 
The formation of benzene may be increased by reducing 
the diazotate with alkaline stannite (Friedlander, Ber, 1889, 
22, 587). . 
Under conditions such as will be described, pure benzene is 
formed by the action of stannic chloride on phenylhydrazine ; 
this can be explained either with the assumption of the inter- 
mediate formation of diazonium chloride or without it. The 
following equation will represent the reaction if diazonium 
chloride is formed :— ; 
RHN.NH, + 2Cl,=RN: NCl+3HCI. 
Now since autoreduction is possible in the case of phenyl- 
hydrazine (Chattaway, Trans. Chem. Soc., 1911, 99, 404), the 
diazonium salt may next take up hydrogen from another 
.molecule of phenylhydrazine :— . 
R 
% 
NeW 
ee a eee 
nN: No! Hi 
Nise oP roel 
H | 
The intermediate formation of diazonium salt is probable, 
considering the explosive violence with which the reaction 
takes place. : 
The other equation that may represent the reaction is— 
C,H. J, De es 
N. N | 
a eae, 
fe ae 
but such behaviour of chlorine of stannic chloride is not ex- 
pected from the existence and properties of the molecular 
compounds of ammonia and stannic chloride, Sn Cl, (NH), 
= O,H,+N,+2HCl. 
