Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 10, pp. 1805−1806.
Pleiades Publishing, Ltd., 2009.
Original Russian Text A.V. Shastin, B.L. Korsunskii, V. P. Lodygina, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 10, pp. 1653−1654.
STUDIES IN THE FIELD OF CHEMISTRY OF NITRO COMPOUNDS
(TO 100TH BIRTHDAY ANNIVERSARY OF S. S. NOVIKOV)
Reactions of 1,1-Diamino-2,2-dinitroethylene
A. V. Shastin, B. L. Korsunskii, and V. P. Lodygina
Institute of Chemical Physics Problems, Russian Academy of Sciences, Chernogolovka, Russia
Received April 29, 2009
Abstract—Reactions of 1,1-diamino-2,2-dinitroethylene with diamines were studied.
1,1-Diamino-2,2-dinitroethylene (I, FOX-7) is
a promising high-density thermally stable power-
consuming compound [1, 2], which can be also of
interest as a mother substance for the synthesis of various
derivatives of 1,1-diaminoethylene. There are some
publications devoted to the chemical transformations
of I [2
7]. In particular, it was shown that compound I
reacts with oxalyl chloride by the both amino groups to
form a corresponding imidazolidinedion , can play
a role of the amine component of Mannich’s reaction ,
is halogenated and nitrated by the nitromethylene group
, is denitrated under the action of peroxoacids , and
reacts with amines and hydrazine with the replacement
of one or two amino groups [6, 7].
Although there are published data on the fact that
compound I reacts with various diamines and hydrazine
[6, 7], no experimental details (reaction conditions such
as solvent, duration, catalytic agent, yield, and product
characteristics) are given in these publications.
To ﬁ nd out how easily these reactions occur, we have
studied the reaction of 1,1-diamino-2,2-dinitroethylene
with 1,2-diaminoethane, 1,3-diaminopropane, and
1,4-diaminobutane. Initial diaminonitromethylene (I)
was synthesized by the nitration of 4,6-dihydroxy-2-
methylpyrimidine (II) (see the scheme).
The results obtained are given in the table where the
yields of the corresponding diamino-derivatives prepared
from 1,1-diiododinitroethylene are shown for comparison
Comparative results of the synthesis of cyclic
dinitroethylenediamines from compound I and