
TY  - JOUR
A1  - Chapman, KJ 
A1  - Dyall, LK 
T1  - Synthesis and characterization of N-Chloro-o-nitroanilines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1976
VL  - 29
IS  - 2
SP  - 367
EP  - 374
KW  - 
UR  - https://doi.org/10.1071/CH9760367 
N2  - Chlorine(1) oxide in carbon tetrachloride was found to be an effective reagent for N-chlorinating 2-nitroanilines. These N-chloro-2-nitroanilines are sufficiently stable in solution at 20º to be characterized by reduction and by proton n.m.r, and infrared spectra. The infrared N-H stretching frequencies fall near the low value of 3330 cm-1, apparently because of interaction between N-H bond and chlorine lone pairs; there are also effects of intramolecular hydrogen bonding and of conformation. Under acid catalysis, N-chloro-2-nitroaniline rearranges to C-chlorinated 2-nitroanilines, while with alkali it cyclizes to benzofuroxan. The acid-catalysed reaction has the same features as the Orton rearrangement of N-chloroacetanilides. 
ER  -

