Synthesis of 3,3-bis(difluoramino)octahydro-1,5,7,7-tetranitro-1,5-diazocine (TNFX), a diversified energetic heterocycle

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• 作者：Axenrod ; Theodore ; Guan ; Xiao-Pei ; Sun ; Jianguang ; Qi ; Lida ; Chapman ; Robert D. ; Gilardi ; Richard D.
• 刊名：Tetrahedron Letters
• 出版年：2001
• 出版时间：April 2, 2001
• 年：2001
• 卷：42
• 期：14
• 页码：2621-2623
• 全文大小：92.3 K

文摘

The syntheses of new 3,3-dinitro derivatives of the 1,5-diazocine ring system are described. Highly deactivated precursor ketones hexahydro-7,7-dinitro-1,5-bis(2- and 4-nitrobenzenesulfonyl)-1,5-diazocin-3(2H)-ones (18) have been difluoraminated to the corresponding gem-bis(difluoramino)diazocines (19). The 1,5-bis(4-nitrobenzenesulfonyl)diazocine derivative undergoes N-nitrolysis with the protonitronium reagent formed in the nitric acid–trifluoromethanesulfonic acid–antimony pentafluoride system to produce 3,3-bis(difluoramino)octahydro-1,5,7,7-tetranitro-1,5-diazocine 2 (TNFX), containing nitramine, gem-dinitro, and gem-bis(difluoramino) structural components.