1
286
LEVANOVA et al.
mixture of 12.43 g (0.2215 mol) of KOH and 55 mL of
hydrazine hydrate (Se : KOH = 1 : 5) at 80–85°С. 1,3-
Dichloropropene 1 (9.83 g, 0.0886 mol) was added at
J. Org. Chem., 2008, vol. 44, no. 4, p. 505. DOI:
0.1134/S1070428008040064.
1
6
7
. Levanova, E.P.,Vakul’skaya, T.I., Shevchenko, S.G.,
Grabel’nykh, V.A, Sukhomazova, E.N., Elaev, A.V.,
Kolesnikov, A.V., Klyba, L.V., Russavskaya, N.V.,
Albanov, A.I., and Korchevin, N.A., Russ. J. Org.
Chem., 2008, vol. 44, no. 10, p. 1422. DOI: 10.1134/
S1070428008100047.
2
5°С and stirred for 11 h at this temperature. The
organic layer was separated and the water-hydrazine
layer was extracted with dichloromethane. The
combined organic fractions were distilled in a vacuum.
Yield 1.52 g (15%, E,Z : E,E : Z,Z = 6.0 : 1.0 : 5.8). bp
–
1
1
(
(
00–105°С (2 mmHg). IR spectrum, ν, cm : 1620
. Grabel’nykh, V.A, Levanova, E.P., Zemirova, I.A.,
Russavskaya, N.V., Klyba, L.V., Shulunova, A.M.,
Albanov, A.I., and Korchevin, N.A., Russ. J. Gen.
Chem., 2012, vol. 82, no. 1, p. 82. DOI: 10.1134/
S1070363212010136.
1
С=С). Н NMR spectrum, δ, ppm: E,Z-isomer: 3.18 d
3
3
2Н, СН -Е, J = 8.0 Hz), 3.33 d (2Н, СН -Z, J =
2
2
8
3
=
.0 Hz), 6.03 m (2Н, ClCH=, =CHCH ); E,E-isomer:
2
3
.14 d (4Н, СН , J = 8.0 Hz), 6.03 m (2Н, ClCH=,
2
3
CHCH ); Z,Z-isomer: 3.40 d (4Н, СН Se, J =
.0 Hz), 6.03 m (2Н, ClCH=, =CHCH2). С NMR
2
2
1
8. Russavskaya, N.V., Grabel’nykh, V.A, Levanova, E.P.,
Sukhomazova, E.N., Klyba, L.V., Zhanchipova, E.R.,
Albanov, A.I., Tatarinova, A.A., Elaev, A.V.,
Deryagina, E.N., Korchevin, N.A., and Trofimov, B.A.,
Russ. J. Org. Chem., 2006, vol. 42, no. 5, p. 652. DOI:
3
8
spectrum, δ, ppm: E,Z-isomer: 18.43 and 22.30 (СН Se,
2
1
1
JСSe 59.2 Hz, J
61.3 Hz), 119.63 and 119.11
СSe
(
2
ClCH=), 128.66 and 130.36 (=CHCH ); E,E-isomer:
2
1
1
01134/S1070428006050022.
2.21 (СН Se, J 62.3 Hz), 119.17 (ClCH=), 130.28
2 СSe
1
(=CHCH ); Z,Z-isomer: 18.40 (СН Se, J = 60.0 Hz),
9. Sadekov, I.D. and Minkin, V.I., Russ. Chem. Rev., 1995,
vol. 64, no. 6, p. 491. DOI: 10.1070/
RC1995v064n06ABEH000162.
2
2
СSe
7
7
1
19.78 (ClCH=), 128.60 (=CHCH2).
Se NMR
spectrum, δ, ppm: 265.3 (Z,Z), 262.4 (Z,E; E,E).
Found, %: С 31.53; Н 3.35. C H Cl Se. Calculated, %:
6
8
2
1
0. Shimizu, T., Kawaguchi, M., Tsuchiya, T., Hirabayashi, K.,
and Kamigata, N., J. Org. Chem., 2005, vol. 70,
p. 5036. DOI: 10.1021/jo0502807.
С 31.33; Н 3.51.
ACKNOWLEDGMENTS
1
1. Levanova, E.P., Grabel’nykh, V.A, Russavskaya, N.V.,
Klyba, L.V., Zhanchipova, E.R., Albanov, A.I.,
Tarasova, O.A., and Korchevin, N.A., Russ. J. Gen.
Chem., 2009, vol. 79, no. 6, p. 1097. DOI: 10.1134/
S1070363209060103.
This work was performed with the use of equip-
ment of the Baikal analytical Center for joint usage of
the Siberian Branch of the Russian Academy of Sciences.
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