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POTAPOV et al.
which enter into nucleophilic substitution and addition
that allows to obtain unsymmetrical tellurides [1, 15].
Organotellurium trihalides add to unsaturated com-
pounds to form unsymmetrical telluranes [15].
Structure of the obtained compounds was studied in
the Baikal Analytical Center for Collective Use of the
Siberian Branch of the Russian Academy of Sciences.
ACKNOWLEDGMENTS
In the literature, there is only one paper [13] de-
scribing the synthesis of vinyltellurium tribromides
and no data exist on the synthesis of bis(2-bromovinyl)-
ditelluride. The reaction of tellurium tetrabromide with
acetylene proceeds stereoselectively as anti-addition to
form E-2-bromovinyltellurium tribromide [13].
This work was supported by the Russian Founda-
tion for Basic Research (grant nos. 12-03-01098 and
11-03-00810).
REFERENCES
1. Zeni, G., Ludtke, D.S., Panatieri, R.B., and Braga, A.L.,
Chem. Rev., 2006, vol. 106, no. 3, p. 1032.
We studied the addition reaction of tellurium
tetrabromide to phenylacetylene, the first example of
the stereoselective synthesis of Z-2-bromo-vinyltellu-
rium tribromide I. Compound II is the first re-
presentative of 2-bromovinyl ditelluride.
2. Potapov, V.A. and Amosova, S.V., Phosphorus, Sulfur,
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To conclude, we have developed effective proce-
dures for the stereoselective synthesis of previously
unknown compounds I and II, which are promising
intermediates for the synthesis of unsaturated organo-
tellurium compounds. Whereas the addition of tellu-
rium tetrabromide to acetylene results in E-2-bromo-
vinyltellurium tribromide [13], the reaction with phenyl-
acetylene proceeds as stereoselective syn-addition to
form the product Z-I.
7. Potapov, V.A., Khabibulina, A.G., Musalova, M.V.,
Chernyshev, K.A., and Amosova, S.V., Zh. Org. Khim.,
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Z-2-Bromo-2-phenylvinyltellurium tribromide (I).
Yellowish powder, mp 159–162°C (decomp.). 1H
NMR spectrun, δ, ppm: 7.53–7.57 m (3Н, Ph), 7.72–
7.76 m (2Н, Ph), 9.56 s (1Н, =СН). 13С NMR
8. Potapov, V.A., Musalova, M.V., Musalov, M.V., and
Amosova, S.V., Russ. Chem. Bull., 2009, vol. 58, no. 11,
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9. Potapov, V.A., Musalova, M.V., and Amosova, S.V.,
1
Russ. Chem. Bull., 2012, vol. 61, no. 1, p. 204.
spectrum, δС, ppm: 125.95 d (=СН, JСТe 219 Hz),
10. Amosova, S.V., Martynov, A.V., Penzik, M.V.,
Makhaeva, N.A., Potapov, V.A., Albanov, A.I.,
Zhilitskaya, L.V., and Voronkov, M.G., J. Organomet.
Chem., 2008, vol. 693, no. 24, p. 3650.
11. Amosova, S.V., Martynov, A.V., Shagun, V.A., Musa-
lov, M.V., Larina, L.I., Krivdin, L.B., Zhilitskaya, L.V.,
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127.83 (Ph), 129.21 (Ph), 131.53 (Ph), 135.47 (Ph),
138.23 (BrC=). 125Te NMR spectrum: δТе 747 ppm.
Found, %: C 17.00; H 1.03; Br 58.78; Te 23.00.
С8Н6Br4Те. Calculated, %: C 17.49; H 1.10; Br 58.18;
Te 23.23.
Z,Z-Bis(2-bromo-2-phenylvinyl)ditelluride (II).
1
Dark red oily substance. H NMR spectrum, δ, ppm:
12. Musalova, M.V., Potapov, V.A., Musalov, M.V., and
Amosova, S.V., Russ. Chem. Bull., 2012, vol. 61, no. 12,
p. 2363.
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Musalov, M.V., and Amosova, S.V., Russ. J. Org.
Chem., 2013, vol. 49, no. 9, p. 1397.
14. Stefani, H.A., Petragnani, N., Zukerman-Schpector, J.,
Dornelles, L., Silva, D.O., and Braga, A.L., J. Organo-
met. Chem., 1998, vol. 562, no. 1, p. 127.
15. Potapov, V.A., Organic Selenium and Tellurium Com-
pounds, vol. 4, Chichester: John Wiley & Sons Ltd,
2013, p. 765.
7.21–7.25 m (3Н, Ph), 7.45–7.49 m (2Н, Ph), 8.21 s
(1Н, =СН). 13С NMR spectrum, δС, ppm: 108.31
(=СН, 1JCTe 334 Hz), 127.09 (Ph), 127.98 (Ph), 128.39
(Ph), 133.34 (BrC=), 138.10 (Ph). 125Te NMR
spectrum: δТе 365 ppm. Found, %: C 31.08; H 1.90; Br
25.42; Te 41.44. С16Н12Br2Те2. Calculated, %: C
31.03; H 1.95; Br 25.81; Te 41.21.
NMR spectra were recorded on a Bruker DPX-400
spectrometer operating at 400.13 (1H), 100.61 (13C),
126.24 MHz (125Te) using DMSO-d6 (I) or CDCl3 (II)
as solvent.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 12 2013