28943-91-1Relevant academic research and scientific papers
Reaction of N-Acyloxy-2-nitrobenzenamines.I. Thermolysis in Benzene or Bromobenzene
Bryant, Ian R.,Dyall, Leonard K.
, p. 2275 - 2288 (2007/10/02)
N-Acyloxy-2-nitro- and N-acyloxy-2,4-dinitro-benzenamines have been pyrolysed at 140 deg C in benzene or bromobenzene solution.Homolysis ( to form RCO2-radical and ArNH-radical) 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 ArNH01+, RCO21- with subsequent transfer of proton, and cyclization of the singlet 2-nitrophenylnitrene.These simple reactions compete with bimolecular 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.
