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 |
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Authors: | A O Finogenov M A Epishina I V Ovchinnikov A S Kulikov I V Anan’ev N N Makhova |
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Institution: | 1.N. D. Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Moscow,Russian Federation;2.A. N. Nesmeyanov Institute of Organoelement Compounds,Russian Academy of Sciences,Moscow,Russian Federation |
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Abstract: | Isomeric 1,3- and 1,4-bis3(4)-nitrofuroxan-4(3)-yl]nitro(dinitro)benzenes were synthe-sized in high yields by nitration of
the corresponding 1,3- and 1,4-bis3(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-nitrofuroxan-3-yl)-4-nitrobenzene was confirmed by X-ray diffraction analysis. 1,3- and 1,4-Bis(3-nitrofuroxan-4-yl)nitrobenzenes
underwent thermal isomerization to more thermodynamically favorable 1,3- and 1,4-bis(4-nitrofuroxan-3-yl)nitrobenzenes. |
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