CHEMISTRY: STIEGLITZ AND COLLABORATORS 207 
stances which could not form simple univalent nitrogen derivatives may 
be rearranged in the same fashion as those which would easily lead to 
such derivatives and the theory of the rearrangements must now count 
with this fact. Whether we actually have a direct exchange of radicles 
(C6H5)2C — NCH3 -> (QH5)C — NCH3 
II II (8). 
C6H5 OH OH CgHs 
as postulated by Beckmann^o for the analogous rearrangement of oximes 
(C6H5)2C :NOH, or whether in both of these cases the rearrangements 
go by way of salts of univalent nitrogen derivatives, will be considered 
in detail in another place. It must suffice to point out here that which- 
ever path the rearrangement follows, the final result is that the positive 
hydroxyl group of the hydroxylamines and of the oximes undoubtedly 
becomes a negative group in the course of the reaction: it still would 
be the unstable radicle in the original molecule and the satisfaction of 
its tendency to become negative would still be the prevaiHng influence 
in the rearrangement (see part I). 
THE REARRANGEMENT OF TRIPHENYLMETHYL AZIDES 
AND OE SYM. DI-TRIPHENYLMETHYLHYDRAZINE 
WITH JAMES KUHN SENIOR 
While there may be some question as to the mechanism of the rear- 
rangement of hydroxylamine derivatives (see above), the theory of a 
direct exchange of radicles (equation 8) would be quite inappHcable to 
the rearrangements of azides. Triphenylmethyl halogen amines and 
hydroxylamines having been found, in this laboratory, to undergo nor- 
mal rearrangements, the problem of the rearrangement of triphenyl- 
methylazides (C6H5)3C.N(N2) was undertaken by us. It was intended 
to settle three main questions. The first two were: (1) Whether a 
rearrangement could be effected at all; (2) Whether heat alone would 
not be sufficient to effect the rearrangement, this being the agent indi- 
cated by the univalent nitrogen theory of the rearrangement: 
(C6H5)3C.N(N2) -N2 -> (C6H5)3C.N -> (C6H5)2C :NC6H5. (9) 
Both of these questions were easily answered in the affirmative. 
When the azide is heated to a high temperature, it is decomposed, with 
a loss of nitrogen. The course of the rearrangement was followed by 
the hydrolysis of the product and identification of the substances thus 
formed, namely anihne and benzophenone. These are the compounds 
which phenylimido benzophenone (C6H5)2C:NC6H5 (equation 9) should 
