Substituent effects in the conversion of azido‐ and diazidotrinitrobenzenes to benzofuroxans and difuroxans

The preparation of a number of substituted dinitrobenzofurazan oxides (dinitrobenzofuroxans) and nitrobenzobis(oxadiozoles) (nitrobenzodifuroxans), in which the substituents were amino, fluoro, formamido, hydroxy, and ureido groups, by thermolysis of azido precursors is described. The ease of thermolysis appears to be an inverse function of the angle of twist of the nitro groups ortho to the azido group from the plane of the benzene ring. Amino‐ and hydroxy‐substituted dinitrobenzofuroxans and nitrobenzodifuroxans were found to be much more stable than their non‐nitro‐substituted counterparts.