452 R. ROBINSON AND H. G. SMITH. 
the molecule follows from the following considerations:— 
In the first place the connection must be with carbon and 
not oxygen, for, otherwise, the production of dinitroveratrol 
would be impossible. This connection may involve either 
the position 4— or 4: 5- (II), but dinitroveratrol would not 
be produced if carbon were attached to the position 3— (or 
6—-) of the veratrolring. It is evident from the ready pro- 
duction of disubstitution derivatives that each nucleus is 
attached in one position only to carbon, and confirmation of 
this statement may be found in the production of 6— bromo- 
veratric acid, unmixed with any isomeride, by the oxidation 
of dibromo-eudesmin by means of potassium permanganate. 
It may also be pointed out that the constitution of dinitro- 
eudesmin is proved by its subsequent conversion to 4: 5— 
dinitroveratrol on boiling with nitric acid. The veratrol 
nuclei both occur, therefore, in the state of combination 
indicated in (III). 
yy, O 
Me O | NOz ‘4 - MeO 
| 
Me O NOz )s MeO 
As 
6 
I. II. III. 
The formula of eudesmin may be written 
Me O OM 
e€ 
Me O Yn Ge eee a O Me 
Pes Me, Nie 
and its conversion to dinitroveratrol is represented in the 
scheme : 
‘ /CO2H. 
Me O ‘ —(CgHsO2)- O Me MeO 
ae 
Me O we OMe MeO st 
/ VA NOe 
NO: 
MeO / 
—> 2 
MeO 
