Abstract
The trinitromethyl group is a highly oxidized group that is found as an active functionality in many high-energy-density materials. The most frequently used previous synthetic method for the introduction of the trinitromethyl group is the nitration of heterocyclic compounds containing an acetonyl/ethyl acetate/chloroxime group. Now a novel strategy for constructing a trinitromethyl group (
5
)
via
nitration of an ethylene bridged compound, dipyrazolo[1,5-
a
:5′,1′-
c
]pyrazine (
2
), is reported. In addition, the other two nitrated products (
3
and
4
) were obtained under different nitrating conditions. Compound
5
has excellent detonation performance (
D
v
= 9047 m s
−1
,
P
= 35.6 GPa), and a low mechanical sensitivity (
IS
= 10 J,
FS
= 216 N), with an especially attractive heat of detonation of 6921 kJ kg
−1
, which significantly exceeds that of the state-of-the-art explosive CL-20 (
Q
: 6162 kJ kg
−1
).
An energetic compound with a trinitromethyl group has been achieved
via
a novel strategy of nitration of an ethylene bridged compound and shows excellent heat of detonation and promising properties.