210 
CHEMISTRY: STIEGLITZ AND COLLABORATORS 
rangement should inevitably follow. Whether this argument should ulti- 
mately be found to be altogether right or not, it is a noetworthy fact 
that it led us to the first realization of the rearrangement of a hydra- 
zine derivative along these Hues. From the product of the action of 
zinc chloride on the symmetrical hydrazine, aniHne was obtained and 
identified (by a positive chloride of Hme test; by analysis of its chloro- 
platinate, which gave 32.80% platinum, theory 32.78%). The question 
as to the mechanism of the rearrangement awaits the identification of 
the further products of the reaction, but aniHne could be formed only 
by a migration of a phenyl group from carbon to nitrogen, the type of 
rearrangement we desired to produce. This is, we beHeve, the first re- 
arrangement of a hydrazine along the fines so characteristic for the 
hydroxylamine derivatives, which have been known for forty years. It 
is significant that the way to its accomplishment was pointed by the 
application of Thomson's original theory of electron valences to the sub- 
ject of these rearrangements. 
1 J. J. Thomson, Electricity and Matter, 1905, and Corpuscular Theory of Matter, 1907. 
2 L. W. Jones, Amer. Chem. J., 50, 440 (1913); Ibid., 48, 1 (1912). 
3 J. Stieglitz and P. N. Leech, /. Amer. Chem. Soc, 36, 272 (1914) and J. Stieglitz, Ber. d. 
Chem. Ges., 43, 782 (1910); 46, 2149 (1913); Amer. Chem. J., 46, 327 (1911). 
* See the bibliography of the theory of the rearrangements, Stieglitz and Leech, loc. cit. 
^ See a preliminary report, J. Stieglitz and Isabelle Vosburgh, Ber. D. chem. Ges., 46, 2151 
(1913); also the following article. 
6 Th. Seliwanow, Ibid., 25, 3617 (1892); F. Lengfeld and J. Stieglitz, Amer. Chem. J., 15, 
215, 504 (1893). 
7 W. A. Noyes, /. Amer. Chem Soc, 23, 450 (1901); J. Stieglitz, Ibid., 23, 796 (1901); 
Walden, Zs. physik. Che?n., 43, 385 (1903). 
8 J. J. Thomson, Phil. Mag., 27, 757 (1914). 
^ A. A. Noyes, Carnegie Inst. Publications, 63, 351 (1907). 
10 W. C. Bray and G. E. K. Branch, /. Amer. Chem. Soc, 35, 1440 (1913). 
" G. N. Lewis, Ibid., 35, 1448 (1913). 
^2 J. Stieglitz and Leech, loc. cit. 
13 J. StiegKtz, /. Amer. Chem. Soc, 30, 1797 (1908). See also W. A. Noyes, loc. cit. 
" For the theory of the intermediate formation of univalent nitrogen derivatives, see J. 
Stieglitz, /. Amer. Chem. Soc, 18, 751 (1896); 29, 49 (1903), and the literature references, 
Stieglitz and Leech, loc. cit. 
IB A. Werner, Ber. D. chem. Ges., 25, 33 (1892); 26, 1562 (1893); 29, 1153 (1896); M. 
Kubara, Mem. Coll. Sci. Engin., Kyoto, 6, 1 (1913). 
16 J. Stieglitz and G. Curme, Ber. D. chem. Ges., 46, 911 (1913). 
17 J. Thiele, Ibid., 44, 2522 (1911). 
18 J. J. Thomson, Phil. Mag., 27, 784 (1914). 
19 J. StiegKtz and P. P. Peterson, Ber. D. chem. Ges., 43, 782 (1910), and P. P. Peterson, 
Amer. Chem. J., 46, 325 (1911). 
^« E. Beckmann, Ber. D. chem. Ges., 19, 988 (1886); 27, 300 (1894). 
21 A. Angeli, Chem. Zentralbl., 1910, II, 861. 
22 A. V. Baeyer, Ber. D. chem. Ges., 32, 3627 (1899). 
