
TY  - JOUR
A1  - Bryant, IR 
A1  - Dyall, LK 
T1  - Reactions of N-Acyloxy-2-nitrobenzenamines. I. Thermolysis in Benzene or Bromobenzene
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1989
VL  - 42
IS  - 12
SP  - 2275
EP  - 2288
KW  - 
UR  - https://doi.org/10.1071/CH9892275 
N2  - N-Acyloxy-2-nitro- and N-acyloxy-2,4-dinitro-benzenamines have been pyrolysed at 140º in benzene or bromobenzene solution. Homolysis (to form RCO2 and ArNH ) is ruled out since virtually all the carboxylate is isolated as carboxylic acid. This acid might arise via a concerted elimination process (the other product being a benzofurazan 1-oxide), or via heterolysis to ArNH+, RCO2- with subsequent transfer of proton, and cyclization of the singlet 2-nitrophenylnitrene. These simple reactions compete with bimolecuiar reactions of products with substrate, in which the corresponding amine, azoxy compound and acid anhydride are generated. Attempts to synthesize N-tosyloxy derivatives of nitrobenzenamines gave only thermal decomposition products. N-Trifluoroacetoxy-2,4-dinitrobenzenamine was isolated as a crude product which detonated violently. 
ER  -

