202 CHEMISTRY: STIEGLITZ AND COLLABORATORS 
The same net result would be shown if the alternative structure 
(C6H5)3C+-NI(++N+++)=N were accepted for the azide.) 
3. Peroxides, in whose rearrangement a positive charge on an oxygen 
atom is converted into a stable negative charge : 
(CH3+)-CK 1 (CH3+)iCK ^ (CH3+)-C C ^ 
(+CH3) (CH3+) 
In conclusion, the effects of an electric current in decomposing the 
salts of organic acids are entirely analogous, fundamentally, to these 
molecular rearrangements. With the current the effect is produced by 
the positive electrode charge, with these compounds, by the positive 
polar charges on the specific atoms, as just shown. 
The original Thomson theory of electron valences is evidently ex- 
tremely useful in the precise formulation of these molecular rearrange- 
ments, involving a large group of organic reactions. Of the newer theo- 
ries of Thomson, Bray and Branch, and Lewis, we find occasion to use 
only so much as is already found in the original theory. This, of course, 
does not exclude the possibility that the newer assumptions may reveal 
their usefulness in other fields of investigation. (Thomson's structure for 
benzene, developed on the basis of the newer theory,i^ interpreted rig- 
orously and without further limiting assumptions, seems to make pos- 
sible at least four di-substitution products C6H4XY, while only the 
three well known series have been recognized.) 
(For references see end of following article.) 
MOLECULAR REARRANGEMENTS OF TRIPHENYLMETHANE 
DERIVATIVES. II. EXPERIMENTAL PART 
By Julius Stieglitz and Collaborators 
KENT CHEMICAL LABORATORY. UNIVERSITY OF CHICAGO 
Read before the Academy, December 9, 1914. Received, February 20, 1915 
MOLECULAR REARRANGEMENTS OF TRIPHENYLMETHYL HALOGEN AMINES^ 
WITH ISABELLE VOSBURGH f AND AGNES FAY MORGAN 
The study of the mechanism of the molecular rearrangement of acyl 
halogen amines RCO.NH(Hal) is compHcated by the fact that the salts 
formed by the bases used as reagents to start the rearrangement may 
t My young collaborator, Miss Vosburgh, who carried out the first part of the experi- 
mental work of this investigation most skilfully and conscientiously, died December 4, 1914, 
as the result of an automobile accident. — J. S. 
