234
KOVAL,
7.1 7.7 and 1.04 ppm We obtained 0.09 g (41%) of diphenyl disulfide
C6H5 and CH2 CH2
(
respectively) and two triplets from groups CH3 (
0.31 ppm) and (CH2)3 ( 3.34 ppm).
identified by melting with an authentic sample.
Similarly was carried out the oxidative benzene-
sulfonylimination of disulfide IId. In this case we
isolated 0.16 g (38%) of sulfinamidine IVb and
0.15 g (50%) of 2,2 -dinitrodiphenyl disulfide
identified by melting with an authentic sample.
The tests for biological activity established that
compound IVb in small concentrations showed a
relatively high fungicidal activity with respect to
spores of fungi Puccinia triticina and a moderate
fungicidal activity against the spores of Phytophtora
infestans.
REFERENCES
1. Koval,, I.V., Goncharuk, V.N., and Oleinik, T.G.,
Zh. Org. Khim., 1993, vol. 29, no. 10, pp. 2002 2007.
2. Koval,, I.V., Usp. Khim., 1994, vol. 63, no. 4,
pp. 338 360.
EXPERIMENTAL
IR spectra were recorded on spectrophotometer
UR-20 from samples pelleted with KBr. H NMR
1
3. Koval,, I.V., Usp. Khim., 1994, vol. 63, no. 9,
pp. 776 792.
spectra were registered on JEOL C-60 instrument at
operating frequency 60 MHz from solutions in
CF3COOH internal reference HMDS, the chemical
shifts were presented in the scale. N-arenesulfenyl-
N,N -bis(arenesulfonyl)sulfinamidines Ia, b were
prepared along procedure described in [13, 14].
4. Koval,, I.V., Zh. Org. Khim., 1996, vol. 32, no. 9,
pp. 1287 1318.
5. Koval,, I.V., Usp. Khim., 1996, vol. 65, no. 5,
pp. 452 473.
6. Koval,, I.V., Usp. Khim., 1995, vol. 64, no. 8,
pp. 781 802.
Disulfides IIa f. To a solution of 0.01 mol of
compound Ia or Ib in 75 ml of anhydrous benzene
was added at vigorous stirring 0.01 mol of an
appropriate sodium thiolate. The reaction mixture
became a solution, and then separated a fine pre-
cipitate. The reaction mixture was stirred for 15
30 min and filtered. Disulfides IIa f were obtained
from the filtrate by evaporation of benzene in air and
crystallization of the residue from an appropriate
solvent (or by a vacuum distillation in the case of
liquid products). The precipitate obtained by filtration
of the reaction mixture was dissolved in 100 ml of
water and filtered. On acidification of filtrate were
precipitated the corresponding sulfinamidines
identified by mixed sample melting point [15].
7. Zefirov, N.S., Zyk, N.V., Beloglazkina, E.K., and
Tyurin, V.S., Izv. Russian Akad. Nauk, Ser. Khim.,
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Oxidative benzenesulfonylimination of unsym-
metrical disulfides IIc, d. To a solution of 0.001mol
of disulfide IIc in 10 ml of pyridine was added
0.002 mol of sodium benzenesulfonylchloroamide,
the mixture was stirred by shaking for 30 min and
then left standing for several hours till negative reac-
tion for active chlorine. The reaction mixture was
poured into 80 ml of 10% hydrochloric acid, the
separated precipitate was filtered off, treated with
20 ml of 10% sodium hydrogen carbonate, and
filtered. On acidifying the filtrate N,N -bis(benzene-
sulfonyl)butanesulfinamidine (IVa) was separated in
amount 0.18 g (45%). The product was identified by
mixed sample melting point, IR, and 1H NMR
spectra. The precipitate filtered off after treating
with sodium hydrogen carbonate was washed with
petroleum ether, dried, and recrystallized from CCl4.
13. Kremlev, M.M., Kodachenko, G.F., Burmistrov, S.I.,
and Koval, I.V., USSR Inventor,s Certificate 245771,
1969. SSSR Byull. Izobr., 1969, no. 20.
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Khim., 1970, vol. 6, no. 3, pp. 485 492.
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19. Kharchenko, A.V., Koval,, I.V., and Kremlev, M.M.,
Zh. Org. Khim., 1977, vol. 13, no. 11, pp. 2385 2388.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 2 2002