BEL’SKIKH et al.
180
(13C), and 376 MHz (19F)], chemical shifts were reported
with respect to TMS (1H, 13C) and CCl3F (19F). Mass
spectra taken in electron impact mode (70 eV) were
measured on instruments GC-MS Shimadzu QP5050A
with direct sample admission into the ion source (IIIc)
or Thermo Trace DSQ II (IIId) from an emulsion of the
sample in DMSO.
The study was carried out under a financial support
of the Russian Foundation for Basic Research (grant no.
07-03-00425).
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4
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[2-(Phenyl)hydrazono](oxo)-λ -sulfane (IIIa).
Yield 0.28 g (90%), mp 98°C (103°C [21]). IR spectrum,
ν, cm–1: 3194 (NH), 1273 (NSO), 1200 (CN), 1082
(NSO).1H NMR spectrum, δ, ppm: 7.06 t (1H, Hp,
J 6.4 Hz), 7.38 m (4H, Ho+m), 12.64 s (1H, NCH).
13C NMR spectrum, δ, ppm: 114.67 (C2,6), 123.60 (C4),
129.39 (C3,5), 141.83 (C1). Mass spectrum, m/z (Irel, %):
154 [M]+· (9.3), 105 [M – HSO]+ (16.3), 77 [Ph]+ (97.7).
11. Galyauskayte, R.Y., Bezdudny, A.V., Michot, C., Ar-
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4
[2-(4-Nitrophenyl)hydrazono](oxo)-λ -sulfane
(IIIb). Yield of pure compound after two-fold recrystal-
lization 0.07 g (17%), t.sublim. 204°C. IR spectrum, ν,
cm–1: 3190 (NH), 1330 (CN), 1200 (NSO), 1080 (NSO).
1H NMR spectrum, δ, ppm: 7.50 d (2H, Hm, J 9.1 Hz),
8.25 d (2H, HO, J 9.0 Hz), 13.14 s (1H, NCH). 13C NMR
spectrum, δ, ppm: 114.60 (C2,6), 125.75 (C3,5), 142.19
(C4), 146.47 (C1). Mass spectrum, m/z (Irel,%): 199 [M]+·
(21.1), 150 [M – HSO]+ (43.9), 122 [150 – N2]+ (90.8).
Found, %: C 36.13; H 2.50; N 20.58; S 16.23.
C6H5N3O3S. Calculated, %: C 36.18; H 2.53; N 21.10;
S 16.10. M 199.18.
4
[2-(2,4-Dinitrophenyl)hydrazono](oxo)-λ -
sulfane (IIIc). Yield 0.38 g (77%), mp 117°C. IR
spectrum, ν, cm–1: 3120 (NH), 1330 (CN), 1220 (NSO),
1
1095 (NSO). H NMR spectrum, δ, ppm: 7.94 d (1H,
H6, J 9.4 Hz), 8.57 d d (1H, H5, J 2.5, 9.3 Hz), 8.88 d
(1H, H3, J 2.4 Hz), 12.55 s (1H, NCH). 13C NMR spec-
trum, δ, ppm: 118.40 (C6), 122.27 (C3), 130.32 (C5),
132.60 (C2), 139.54 (C4), 140.85 (C1). Mass spectrum,
m/z, (Irel, %): 244 [M]+· (11.6), 195 [M – HSO]+ (47.4),
168 [C6H4(NO2)2]+ (8). Found, %: C 29.81; H 1.66;
N 22.48; S 12.66. C6H4N4O5S. Calculated, %: C 29.51;
H 1.65; N 22.94; S 13.13. M 244.18.
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me, J.-P., J. Org. Chem., 1979, vol. 44, p. 1181.
22. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E.,
Robb, M.A., Cheeseman, J.R., Montgomery, J.A. Jr., Vre-
ven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyen-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 2 2009