Synthesis of isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan- 4(3)-yl]nitrobenzenes by nitration of the corresponding isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes

摘要

Isomeric 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]nitro(dinitro)benzenes were synthesized in high yields by nitration of the corresponding 1,3- and 1,4-bis[3(4)-nitrofuroxan-4(3)-yl]benzenes with a mixture of 100% nitric acid and concentrated sulfuric acid. The influence of 3- and 4-nitrofuroxanyl fragments on the regioselectivity of the nitration was revealed. The structure of 1,3-bis(4-mtrofuroxan-3-yl)-4-nitrobenzene was confirmed by X-ray diffraction analysis. 1,3- and l,4-Bis(3-nitrofuroxan-4-yl)nitrobenzenes underwent thermal isomerization to more thermodynamically favorable 1,3- and l,4-bis(4-nitrofuroxan-3-yl)nitrobenzenes.