SPECIFIC FEATURES OF REACTION
1203
hydrous ether. In 1 min the solvent was evaporated,
the oily residue was treated with a mixture ethanol
ether. We obtained orange crystals of compound VI,
yield 0.059g (16%), mp88 89 C. Found, %: C 53.58;
H5.50; N 23.35. C8H9N3O2. Calculated, %: C 53.63;
H 5.02; N 23.46.
(b) Under similar conditions the same compound
was prepared from morpholinonitroethene V, yield
70%. The mixed sample of compounds obtained by
procedures (a) and (b) melted without depression of
the melting point.
1H NMR spectra were registered on spectrometer
Bruker AC-200 (200 MHz), internal reference HMDS.
IR spectra were recorded on spectrophotometer
Specord 75IR from solutions in chloroform. UV
spectra were measured on spectrophotometer SF-121.
Mass spectrum was obtained on MKh 1321 instru-
ment (direct admission of the sample into the ion
source, ionizing voltage 70 V, ionizing chamber
temperature 180 C).
(b) In the same fashion at 18 20 C was carried out
a reaction with 1-nitro-1-phenyl-2-p-chlorophenyl-
thioethene (III). The reaction mixture acquired the
characteristic odor of p-chlorophenylthiol. In 10 min
orange crystals of VI were filtered off, yield 0.259 g
(72%).
(c) Ethene VI was also obtained from 2-(benzo-
thiazol-2-yl)thio-1-nitro-1-phenylethene (IV) along
procedure (b) in 53% yield. Mixed samples from
compounds prepared by procedures (b) and (c) with
that prepared by procedure (a) melted without de-
pression of the melting point. The identity of these
compounds was also proved by TLC on Silufol
UV-254 plates,eluent hexane acetone, 2: 1.
REFERENCES
1. Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M.,
and Efremov, D.A., Nitroalkenes. Conjugated Nitro
Compounds, London: J. Wiley, 1994.
2. Kuz,mina, N.V., Lipina, E.C., Kropotova, T.Yu.,
Berkova, G.A., and Pavlova, Z.F., Zh. Org. Khim.,
2001, vol. 37, p. 1327.
1,2-Dihydrazin-1,2-diphenylethene (VII). (a) To
a dispersion of 0.27 g (1 mmol) of dinitrostilbene (II)
in 10 ml of ether was added a solution of 1 ml
(20 mmol) of hydrazine hydrate in 10 ml of ethanol.
In 20 min all the initial ethene dissolved. On remov-
ing the solvent the colorless amorphous residue was
separated on a porous tablet, yield 0.2 g (85%),
mp 94 97 C. Found, %: C 70.42; H 6.56; N 22.89.
C14H16N4. Calculated, %: C 70.00; H 6.67; N 23.33.
M 240. Mass Spectrum: 240 M+ , 224 [_NH2], 209
[_NH], 193 [_NH2], 178 [_NH], 119 [PhCNHNH2],
89 [PhC], 77 [Ph].
3. Pavlova, Z.F., Lipina, E.C., Kasem, Ya.A., Kuz,mi-
na, N.V., Zh. Org. Khim., 1999, vol. 35, p. 1352.
4. Fetell, A.I. and Feuer, H.J., Org. Chem., 1978,
vol. 43, p. 497.
5. Chiara, H., Gomez-Sanchez, A., and Bellanato, J.J.,
J. Chem. Soc., Perkin Trans. II, 1992, p. 787.
6. Paperno, T.Ya. and Perekalin, V.V., Infrakrasnye
spektry nitrosoedinenii (IR Spectra of Nitro Com-
pounds). Leningrad, 1974, p. 46.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 8 2003