136 REPORTS ON THE STATE OF SCIENCE.—1913. 
1-Isopropyleyclohexan-3-ol and 1-isopropylcyclohexan-3-one have 
been prepared, and it is intended to use them as starting-points for the 
preparation of several meta-terpene derivatives. 
The Transformation of Aromatic Nitroamines and Allied Sub- 
stances, and its Relation to Substitution in Benzene Deriva- 
tives.—Report of the Committee, consisting of Professor 
F. §. Kreptna (Chairman), Professor K. J. P. Orton 
(Secretary), Dr. S. RUHEMANN, and Dr. J. T. HEwItt. 
The Transformation of Acetylchloroaminobenzenes and the Chlorination 
of Anilides. The Reactions of Chloroamines in Aqueous Solution. 
[With W. H. Gray, B.Sc.] 
In a previous report,! we have given a summary of the results of a large 
number of experiments on the transformations of chloroamines into the 
isomeric chloroanilides : Ar. NC]. Ac +Cl Ar. NH. Ac; it was shown that 
this change could not be regarded as an intramolecular rearrangement, but 
consisted primarily of a reversible reaction of hydrogen chloride with the 
chloroamine: thus, 
Ar.NCl. Ac-+ HCl +Ar.NH.Ac+ Cl,>ClAr.NH. Ac-+ HCl, 
followed by a direct irreversible interaction of chlorine and the anilide. 
In these experiments the medium was aqueous acetic acid containing 
not less than 50 per cent. of acetic acid. We have now examined the 
behaviour of acetylchloroaminobenzene in pure aqueous solution, and have 
discovered an interesting modification of the ordinary reaction. 
The production of hydrogen chloride during the transformation of a 
chloroamine, in the presence of hydrogen chloride, was first indicated by 
Blanksma,? who found that the amount of this acid at the end of the 
reaction was slightly greater than that originally introduced. Moreover, 
it was demonstrated by Chattaway and Orton’ that any change of the 
chloroamine which occurred in the presence of other acids—for example 
sulphuric—was invariably accompanied by the appearance of hydrogen 
chloride. The first quantitative experiments were made by Orton and 
Jones (compare Reports, 1910). These were carried out in an acetic acid 
medium containing from 0-35 per cent. of water, both in the presence and 
absence of various acids. The following table shows some of the results :— 
TABLE I. 
. . . . Chloroamine Chloroamine 
Medium Acid Time of Reaction Ditappeseed Rednsad 
Per cent. Days Per cent. Per cent. 
65 HA none 22 | 50-8 6-04 
3 H,S0, 13 | 49-16 11-2 
5 HNO, 7 54-96 3°72 
9 HClO, 9 | 48-0 18-67 
* Reports, 1910. 
2 Recueil des Trav. Chim. 1903, 22, 290. 
3 Proc. Chem. Soc. 1902, 18, 200. 5 
