(179) 
compound is unstable and is spontaneously converted into p-chloro- 
acetanilide. A closer investigation showed me that the cause of this 
must be attributed to the action of sunlight. After 14 days exposure 
to the light (May 14-28), the atmosphere being cloudy, this substance 
was entirely converted into p-chloroacetanilide while on a brieht 
day in June the conversion was complete in a day. In the same 
manner it was shown that the analogous bromo-compound C, H, N 
Br CO CH, had been entirely converted after 3—4 hours exposure 
to direct sunlight on an afternoon in June and in 70 hours by exposure 
to imeandescent gaslight; in diffuse daylight the conversion was 
complete after a few days, while both the cblorine and the bromine 
compound, could be preserved unaltered in the dark. 
We therefore see that Br and Cl linked to N, shift to the nucleus 
under the influence of light. On consulting the literature it was 
found that Bamprrenr’) had already shown that phenylnitramine is 
converted by sunlight into o- and p-nitraniline, while he had also 
found that nitrosophenylhydroxylamine is very rapidly decomposed 
by direct sunlight and sometimes even explodes. The reaction takes 
here a more complicated course, the first stage of the reaction is 
probably the migration of the NO group to the nucleus. 
Reeently KNiPscHrer *) has shown that azoxybenzene is converted 
by direct sunlight into 0-oxyazobenzene. 
We therefore see that under the influence of sunlight Br, Cl, NO,, 
NO and O attached to N migrate from the side-chain to the nucleus 
and change place with an atom of hydrogen *), 
In the previous communication (Le.) attention was called to the 
analogy of the CH,-group with NH, and OH. Now however, we 
notice a difference. Whereas sunlight promotes the entering of atoms 
or groups into the nucleus of the NI,-derivatives, it causes the for- 
mation of Brand Cl compounds in the side-chain of the CH,-derivatives, 
for instance in the bromination or chlorination of toluene *). | 
We may briefly refer to the experiments of Srprk *) and Errara ®) 
who have proved that on chlorinating parabromotoluene p-bromo- 
1) Berichte 27, 364, 1554, 34, 66. 
2) Proc. 31 May 1902. 
3) No experiments showing the effect of light have, as yet, been made with 
phenol derivatives containing atoms or groups attached to the oxygen, It is probable 
that sunlight will in this case also excercise an influence on the migration of atoms 
or groups of the side-chain to the nucleus. This should be borne in mind when 
preparing these compounds. 
4) Scuramm, Ber. 18, 608. 
5) Monatsch. f. Chem. 11, 431. 
6) Gazz. Chim. Ital. 17, 202, 
