Efficient Construction of Energetic Materials via Nonmetallic Catalytic Carbon-Carbon Cleavage/Oxime-Release-Coupling Reactions

Journal of the American Chemical Society
Gang ZhaoJean'ne M Shreeve

Abstract

The exploitation of C-C activation to facilitate chemical reactions is well-known in organic chemistry. Traditional strategies in homogeneous media rely upon catalyst-activated or metal-mediated C-C bonds leading to the design of new processes for applications in organic chemistry. However, activation of a C-C bond, compared with C-H bond activation, is a more challenging process and an underdeveloped area because thermodynamics does not favor insertion into a C-C bond in solution. Carbon-carbon bond cleavage through loss of an oxime moiety has not been reported. In this paper, a new observation of self-coupling via C-C bond cleavage with concomitant loss of oxime in the absence of metals (either metal-complex mediation or catalysis) results in dihydroxylammonium 5,5-bistetrazole-1,10-diolate (TKX-50) as well as N, N'-([3,3'-bi(1,2,4-oxadiazole)]-5,5'-diyl)dinitramine, a potential candidate for a new generation of energetic materials.

Citations

Jul 16, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jinhao ZhangQingchun Zhang
Dec 12, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Chengming BianZhongliang Xiao
Apr 29, 2021·The Journal of Physical Chemistry. a·Dmitry V KhakimovNina N Makhova
Nov 6, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Pengju YangGuangbin Cheng

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