2490
EGOROVA et al.
using a rider model under isotropic approximation.
The calculations were performed using software [34].
150 mL of DMSO. The mixture was stirred during 30
min in the dark. The precipitate was filtered off and
washed with DMSO (3×5 mL). After the solvent
evaporation, 0.71 g (89%) of compound 4 was
isolated, mp 152°С (decomp.). IR spectrum, ν, cm–1:
3084, 3016, 2946, 2844, 1594, 1578, 1472, 1432,
1342, 1261, 1107, 1020, 889, 830, 776, 740, 711, 677,
665, 589. Found, %: С 52.29; Н 5.139. C24H27O7Sb.
Calculated, %: С 52.48; Н 4.959.
Major crystallographic parameters of compounds 3
and 4, experimental data, and parameters of the
structure refinement were deposited in The Cambridge
Crystallographic Data Centre [CCDC 1468102 (3) and
1468103 (4)].
Tris(2,6-dimethoxyphenyl)antimony (1). 6.50 g
of antimony(III) chloride (0.03 mol) in 100 mL of
anhydrous diethyl ether was added to an ethereal
solution of 2,6-dimethoxyphenyllithium prepared [35]
from 13.8 g (0.10 mol) of 1,3-dimethoxybenzene and
0.10 mol of phenyllithium. The mixture boiled up, and
white precipitate was formed. After addition of
antimony(III) chloride, the reaction mixture was stirred
during 2 h, excess of 2,6-dimethoxyphenyllithium was
decomposed with 5 mL of water, and the solution was
filtered. Ether was evaporated off on a water bath, and
the residue was poured onto a Petri dish. After the
solvent evaporation, 10.9 g (72%) of compound 1 was
isolated, mp 162°С. IR spectrum, ν, cm–1: 3070, 3056,
2993, 2934, 2828, 1579, 1569, 1462, 1423, 1300,
1234, 1168, 1101, 1041, 1022, 763, 737, 707, 589.
Found, %: С 54.23; Н 4.93. C24H27О6Sb. Calculated,
%: С 54.06; Н 5.10.
ACKNOWLEDGMENTS
Authors acknowledge F.M. Dolgushin (Nesmeyanov
Institute of Organoelement Compounds) for X-ray
diffraction analysis.
REFERENCES
1. Nomura, R., Nakano, T., Yamada, Y., and Matsuda, H.,
J. Org. Chem., 1991, vol. 56, no. 12, p. 4076. doi
10.1021/jo00012a058
2. Nomura, R., Hasegawa, Y., Ishimoto, M., Toyosaki, T.,
and Matsuda, H., J. Org. Chem., 1992, vol. 57, p. 7339.
doi 10.1021/jo00052a060
3. Nomura, R., Miyazaki, S.-I., Nakano, T., and Matsuda, H.,
Chem. Ber., 1990, vol. 123, p. 2081. doi 10.1002/
cber.19901231023
4. Nomura, R., Miyazaki, S.-I., Nakano, T., and Matsuda, H.,
Appl. Organomet. Chem., 1991, vol. 5, p. 513. doi
10.1002/aoc.590050609
5. Monagle, J., J. Org. Chem., 1962, vol. 27, no. 11,
p. 3851. doi 10.1021/jo01058a022
6. Maerov, S., J. Polym. Sci. Polym. Chem., 1979, vol. 17,
Tris(2,6-dimethoxyphenyl)antimony dibromide (2).
0.48 mL of bromine (9.38 mmol) in 50 mL of CCl4
was added to a solution of 5.00 g (9.38 mmol) of
compound 1 in 150 mL of CCl4. The precipitate was
filtered off, washed with diethyl ether (3×5 mL), and
dried. Yield 6.1 g (94%), mp 174°С. IR spectrum, ν,
cm–1: 2997, 2963, 2936, 2833, 1586, 1571, 1475, 1426,
1257, 1172, 1107, 1034, 774, 743, 708. Found, %: С
41.77; Н 3.70; Br 23.24. C24H27Br2О6Sb. Calculated,
%: С 41.59; Н 3.92; Br 23.06.
p. 4033. doi 10.1002/pol.1979.170171223
7. Nomura, R., Ninagawa, A., and Matsuda, H., J. Org.
Chem., 1980, vol. 45, p. 3735. doi 10.1021/jo01307a002
8. Nomura, R., Yamada, Y., and Matsuda, H., Appl.
Organomet. Chem., 1988, vols. 2–6, p. 557. doi
10.1002/aoc.590020610
9. Nomura, R., Yamada, Y., and Matsuda, H., Appl.
Organomet. Chem., 1989, vols. 3–4, p. 355. doi
10.1002/aoc.590030410
10. Nomura, R., Hisada, H., Ninagawa, A., and Matsuda, H.,
Macromol. Chem. Rapid Commun., 1980, vol. 1, p. 135.
doi 10.1002/marc.1980.030010301
11. Nomura, R., Shiomura, Y., Ninagawa, A., and Matsuda, H.,
Macromol. Chem., 1983, vol. 184, p. 1163. doi 10.1002/
macp.1983.021840605
12. Nomura, R., Wada, Y., and Matsuda, H., Polymer
Chem., 1988, vol. 26, p. 627. doi 10.1002/
pola.1988.080260226
Tris(2,6-dimethoxyphenyl)antimony diisocyanate
(3). A suspension of 0.43 g (2.88 mmol) of silver
isocyanate in 150 mL of acetone [36] was added to a
solution of 1.00 g (1.44 mmol) of compound 2 in
the same solvent [36]. Precipitated silver bromide was
filtered off and washed with acetone (3×5 mL). After
the solvent evaporation, 0.88 g (95%) of compound 3
was isolated, mp 142°С. IR spectrum, ν, cm–1: 3007,
2967, 2938, 2835, 2359, 2341, 2189, 1587, 1472,
1425, 1302, 1292, 1255, 1173, 1107, 1030, 899, 773,
744, 711, 617, 594.
Tris(2,6-dimethoxyphenyl)antimony oxide (4).
0.50 g (2.16 mmol) of silver oxide [37] was added to a
solution of 1.00 g (1.44 mmol) of compound 2 in
13. Nomura, R., Wada, T., Yamada, Y., and Matsuda, H.,
Chem. Lett., 1986, no. 11, p. 1901. doi 10.1246/cl.1986.1901
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 11 2016