Synthesis and Characterization of 1,2,3,4-Cyclobutanetetranitramine Derivatives

Abstract

A series of new nitramines have been synthesized. All of the new compounds possess four nitramine moieties arranged about a cyclobutane ring in a 1α,2α,3β,4β (cis,trans,cis) configuration. One of the new materials, 1, is unusually thermally and hydrolytically stable but sensitive to impact. 1,2,3,4-Cyclobutanetetranitramine (3) is reported for the first time.

On the molecular origin of the sensitivity to impact of cyclic nitramines

“…Models A1 and B1 does not reproduce exactly the behavior discussed in the last paragraph in case of those strained nitramines, but the results are comparable. The h 50 value of CBTN is slightly higher than for TNTriCB and about twice the TNCB value, resulting in disagreement with the trend suggested by Chapman …”

“…Given that larger h 50 values indicate more insensitive materials, for the strained‐ring CBTN molecule smaller values were expected than those predicted by aromatic model 1 because, according to Chapman and coworkers, this molecule would be the most sensitive derivative of the nitramines investigated by his group (CBTN, TNCB, and TNTriCB) . The h 50 value of CBTN, according to aromatic model 1, is considerably larger as compared to those of TNTriCB and TNCB (Table ).…”

“…We could gather h 50 values in centimeter measured with two similar approaches: five (TNCB, TNTriCB, CL20, DINGU, and TNAZ) out of the six molecules were obtained using the ERL Type 12 tooling with 2.5 kg impact hammer protocol . The TEX molecule, which was not included in the training group (see below), had its h 50 value also measured by a drop test using similar determination parameters .…”

“…Therefore, we used a set of six h 50 values. In the next section, we present and discuss the results of our models using the six h 50 values in centimeter …”

2,2‐Bis(methoxy‐NNO‐azoxy)ethyl Derivatives of 4,8‐Dihydro‐bis‐furazano[3,4‐b:3′4′‐e]pyrazine: The Synthesis and X‐ray Investigation

“…Both independent molecules adopt nearly the same structure. Central tricyclic skeleton is planar as was earlier observed for other its structurally characterized derivatives ,. The methoxy‐ NNO‐ azoxy fragments adopt nearly planar structure and oriented nearly perpendicularly to each other in both CH 2 CH(N(O)=NOCH 3 ) 2 moieties.…”