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

Author:
Zhao, Gang, He, Chunlin, Yin, Ping, Imler, Gregory H., Parrish, Damon A., Shreeve, Jean’ne M.
Source:
Journal of the American Chemical Society 2018 v.140 no.10 pp. 3560-3563
ISSN:
1520-5126
Subject:
carbon-hydrogen bond activation, catalytic activity, chemical bonding, chemical reactions, cleavage (chemistry), dinitramine, metals, moieties, organic chemistry, thermodynamics
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.
Agid:
6033141