ox DY^fAMIC ISOMEHlfeM. 159 



(tfi-sevics are able to pass not only into stereoisomeric a'fi compounds 

 but also into isomeric sulpholactoucs. A number of the latter have been 

 examined and described. 



The expenses incurred in connection with investigations described 

 above were in part defrayed by a grant made to the Committee in 1904. 

 It is proposed during the coming year to undertake a detailed examination 

 of the optical properties of nitrocamphor and other compounds which 

 exhibit dynamic isomerism in solution. In particular it is proposed to 

 test Biot's hypothesis that anomalous rotatory dispersion is due to the 

 presence in solution of two modifications of a substance — a suggestion 

 which was made some years before the phenomena of dynamic isomerism 

 were clearly understood. 



The Transformation of Aromaiic Nitroamines aiul Allied Substances, 

 and its lielation to Stihstiintiun t?i Ben::enc Derivatives. — Rejiort oj 

 the Committee, coni^iMing of Professor F. S. Kipping (Chairnum), 

 Professor K. J. P. Orton (Secretarij), Dr. S. Ruhemann, Dr. A. 

 Lapwukth, and Dr. J. T, Hewitt. 



I. Nilromnines. 



In continuation of previous work on the transformations of aromatic 

 nitroamines ^ a study of the reactions of s4ribromonitroauiinubenzene has 

 been undertaken. 



Under conditions which lead to the isomeric change of unsubstituted 

 nitroaminobenzenes, that is, treatment with sulphuric acid in acetic acid 

 solution, the .'<-tribromonitroamine is largely converted into 2 : 6-dibromo- 

 •1-nitroaniline, a bromine atom being displaced from the para position by 

 the nitro group. If the reaction, however, is carried out under narrowly 

 defined conditions, namely, in a mixture of acetic acid 2 parts ami 

 sulphuric acid 1 part, which contains 1-") per cent, of water (this 

 proportion of water is essential), other changes are observed, bromo- 

 phcnyliminoquinones, derivatives of the compound, 



-<: 





being formed. s-Tribroaionitroaminobenzene behaves in this respect as does 

 5-trichloronitroamiiiobenzeno, which yields hcxachlorupheuyliminoquinone 5 

 but in the case of ^-trichloronitroaminobenzene a chlorine atom is not 

 displaced by the nitro-group from the para position, and conseijuently no 

 dichloronitroaniiine is formed. 



In contrast to the s-trichloro-aualogue, which yields only one phcnyl- 

 iminoijuinonc, the tribromonitroaminobenzcnc gives a mixture of a penta- 

 and hexa-bromophenyliminoquinone ; the former melts at 170°, and on 

 reduction is converted into a pentabromohydroxydiphenylaminc, juelting 

 at 150° ; and the latter melts at 135°, and yields a hexabromohydroxy- 

 diphenylamine, melting at 207". 



' See Report, 1905, and compare Ortan, Ti-ans. Chem. Svc, 81, 80G ; and Ortoti 

 and Smith, ibid., 87, ^89, 



