MARTYNOV et al.
1252
(C=). 125Te NMR spectrum (DMSO-d6): δTe 723.5 ppm
(δTe 724 ppm [1]).
(=CHTe, JCH = 173.6, JCH = 4.2 Hz), 131.58 d.t
1
3
1
3
(=CHCl, JCH = 204.2, JCH = 5.8 Hz), 135.08 s (=C),
135.08 s (=C). 125Te NMR spectrum (CDCl3):
δTe 635.4 ppm. Found, %: C 20.30; H 1.85; Cl 41.12;
Te 36.46. C6H6Cl4Te. Calculated, %: C 20.74; H 1.74;
Cl 40.81; Te 36.72. M 347.52.
[(Z)-1,3-Dichloroprop-1-en-2-yl][(Z)-2,3-dichloro-
1
prop-1-en-1-yl]tellurium dichloride (4). H NMR
spectrum, δ, ppm: in CDCl3: 4.38 s [2H, =C(Cl)CH2],
5.02 d [2H, =C(Te)CH2], 7.33 s (1H, =CHCl), 7.86 t
(1H, =CHTe); in DMSO-d6: 4.73 s [2H, =C(Cl)CH2],
4.95 s [2H, =C(Te)CH2], 7.66 s (1H, =CHCl), 8.32 s
(1H, =CHTe). 13C NMR spectrum (DMSO-d6), δC,
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 14-03-00185).
1
3
ppm: 46.95 t.d [=C(Te)CH2, JCH = 156.1, JCH
=
=
1
3
REFERENCES
4.0 Hz], 47.25 t.d [=C(Cl)CH2, JCH = 157.0, JCH
1
3
4.0 Hz], 129.28 d.t (=CHTe, JCH = 188.3, JCH = 4.0,
1JCTe = 300.8 Hz), 138.12 d.t (=CHCl, JCH = 206,
1
1. Potapov, V.A., Khabibulina, A.G., Musalova, M.V.,
Chernyshev, K.A., and Amosova, S.V., Russ. J. Org.
Chem., 2014, vol. 50, p. 150.
2. Martynov, A.V., Larina, L.I., and Amosova, S.V., Tetra-
hedron Lett., 2012, vol. 53, p. 1218.
3. Amosova, S.V., Musalov, M.V., Martynov, A.V., and
Potapov, V.A., Russ. J. Gen. Chem., 2011, vol. 81,
p. 1239.
3JCH = 6, JCTe = 35.3 Hz), 143.04 s (=C, JCTe
=
2
2
44.4 Hz), 143.43 s (=C). 125Te NMR spectrum
(DMSO-d6): δTe 847.0 ppm. Found, %: C 17.10;
H 1.48; Cl 50.52; Te 30.76. C6H6Cl6Te. Calculated, %:
C 17.22; H 1.45; Cl 50.84; Te 30.50.
Reduction of isomeric bis(dichloropropenyl)-
tellurium dichlorides 3 and 4. A solution of 1.467 g
(6.6 mmol) of Na2S2O5 in 7 mL of water was added to
a solution of 0.274 g (0.65 mmol) of isomer mixture
3/4 in 5 mL of benzene, and the mixture was stirred for
5 h at room temperature. The mixture was treated with
10 mL of water and extracted with chloroform, and the
extract was dried over CaCl2 and evaporated to isolate
0.170 mg (75%) of a mixture of compounds 5 and 6 at
a ratio of 3:2 (1H NMR).
4. Martynov, A.V. and Amosova, S.V., Russ. J. Gen.
Chem., 2008, vol. 78, p. 2067.
5. Amosova, S.V., Martynov, A.V., Shagun, V.A., Musa-
lov, M.V., Larina, L.I., Krivdin, L.B., Zhilitskaya, L.V.,
and Voronkov, M.G., J. Organomet. Chem., 2008,
vol. 693, p. 2509.
6. Stothers, J.B., Carbon-13 NMR Spectroscopy, New
York: Academic, 1972.
7. Kalabin, G.A., Kushnarev, D.F., and Valeev, R.B.,
Zh. Org. Khim., 1981, vol. 17, p. 1139.
Bis[(Z)-2,3-dichloroprop-1-en-1-yl] telluride (5).
1H NMR spectrum (CDCl3), δ, ppm: 4.26 s (4H, CH2),
7.28 s (2H, =CHTe); published data [1]: 4.24 s (4H,
CH2), 7.25 s (2H, =CH). 13C NMR spectrum (CDCl3),
8. Luthra, N.P. and Odom, J.D., The Chemistry of Organic
Selenium and Tellurium Compounds, Patai, S. and
Rappoport, Z., Eds., Chichester:. Wiley, 1986, vol. 1,
p. 189.
1
3
δC, ppm: 48.45 t (CH2, JCH = 154.2, JCH = 4.0 Hz),
1
9. Laali, K., Chen, H.Y., and Gerzina, R.J., J. Org .Chem.,
108.12 d (=CHTe, JCH = 171 Hz), 135.08 s (=C);
1987, vol. 52, p. 4126.
published data [1]: 48.21 (CH2), 107.83 (=CHTe,
1JTeC = 294 Hz), 131.52 (=C). 125Te NMR spectrum
(CDCl3): δTe 525.1 ppm (δTe 528 ppm [1]).
10. Zhou, Zh.-L., Huang, Y.-Z., Tang, Y., Chen, Zh.-H.,
Shi, L-P., Jin, X.-L., and Yang, Q.-C., Organometallics,
1994, vol. 13, p. 1575.
(Z)-1,3-Dichloroprop-1-en-2-yl (Z)-2,3-dichloro-
prop-1-en-1-yl telluride (6). H NMR spectrum
11. Breitmaier, E., Structure Elucidation by NMR in
Organic Chemistry: a Practical Guide, Chichester, UK:
Wiley, 2002, 3rd ed., p. 26.
12. Petragnani, N., Mendes, S.R., Claudio, C., and
Silveira, C.C., Tetrahedron Lett., 2008, vol. 49, p. 2371.
13. Brandsma, L., Preparative Acetylenic Chemistry,
1
(CDCl3), δ, ppm: 4.27 s [2H, =C(Te)CH2], 4.63 s [2H,
=C(Cl)CH2], 6.84 s (1H, =CHCl), 7.30 s (1H, =CHTe).
13C NMR spectrum (CDCl3), δC, ppm: 48.45 t.d
1
3
[=C(Te)CH2, JCH = 154.2, JCH = 4.0 Hz], 47.33 t.d
1
3
[=C(Cl)CH2, JCH = 153.7, JCH = 8.4 Hz], 110.00 d.t
Amsterdam: Elsevier, 1988, 2nd ed., p. 254.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 9 2015