1
962
VLASOVA et al.
the formation of four-centered intermediate complex,
in the case of triethylsilylmethyl propyl sulfide the
steric effect of bulky triethylsilyl group will prevent
the formation of such complex with the coordination
center at the methyl carbon atom.
volatile fraction collected in the trap propyl iodide was
identified by GLC and IR spectroscopy. IR spectrum,
–
1
ν, cm : 480 (СН I).
2
Reaction of triethylsilylethyl propyl sulfide with
acetyl iodide. Under similar reaction conditions, from
a mixture of 5.4 g (25 mmol) of triethylsilylethyl
propyl sulfide and 4.2 g (25 mmol) of acetyl iodide we
obtained 4.4 g (46%) of [Et Si] O, bp 84–87°C (5 mm
Triethylsilylmethyl propyl sulfide. To sodium
mercaptide prepared from 3.9 g (51 mmol) of pro-
panethiol and 1.8 g of sodium in diethyl ether was
added 8.4 g (51 mmol) of Et SiCH Cl. The reaction
3
2
2
0
20
D
Hg), n 1.4370 (bp 60°С (1 mm Hg), n 1.4340 [4]).
IR spectrum, ν, cm : 1065 (Si–O–Si). Found, %: С
58.80; Н 12.17; Si 21.26. С H ОSi . Calculated, %:
3
2
D
–
1
was carried out at 45–55°C for 7 h. The precipitate was
filtered off, washed with diethyl ether. The ether
extract was evaporated, and residue was distilled in a
1
2
30
2
С 58.54; Н 12.20; Si 22.76. In a volatile fraction
collected in the trap propyl ethanethioate was iden-
tified by GLC and IR spectroscopy. IR spectrum, ν,
2
0
vacuum. Yield 1.1 g (13%), bp 80°C (5 mm Hg), n
1
D
–
1
.4692. IR spectrum, ν, cm : 1695 (S–С=О), 1457 (S–
–
1
СH ), 737–763 (Si–CH ). Found, %: С 59.16; Н 11.93;
cm : 1695 (S–C=O).
2
2
S 14.24; Si 12.74. С H SSi. Calculated, %: С 58.82;
Н 11.76; S 15.69; Si 13.73.
10
24
The IR spectra were recorded on a UR-20
spectrometer in a thin layer. Analysis of the reaction
mixture by GLC was performed on a LKhM-8MDII
instrument equipped with a thermal conductivity
detector, carrier gas – helium, column 1000×4 mm,
sorbent – Chromaton N-AW-HMDS (0.2–0.25 mm,
impregnation with 5% SE-30).
Triethylsilylethyl propyl sulfide. A mixture of 4.3 g
(
57 mmol) of propanethiol and 8.0 g (57 mmol) of
triethylvinylsilane was irradiated with UV light in a
quartz flask with stirring for 10 h. Yield 5.1 g (55%),
2
0
–1
bp 87°C (5 mm Hg), n 1.4750. IR, ν, cm : 1695
D
(
С=О), 1249 [δ(СH ) –Si], 837, 757 [СH ) –Si].
3 3 3 3
REFERENCES
Found, %: С 60.17; Н 11.67; S 14.33; Si 12.05.
С H SSi. Calculated, %: С 60.55; Н 11.93; S 14.68;
Si 12.84.
1
2
3
.
.
.
Vlasova, N.N., Grigor’eva, O.Yu., and Voronkov, M.G.,
Russ. J. Org. Chem., 2013, vol. 49, no. 1, p. 46.
Noller, D.C. and Post, H.W., J. Org. Chem., 1952,
1
1
26
Reaction of triethylsilylmethyl propyl sulfide
vol. 17, p. 1393 .
with acetyl iodide. A mixture of 1.1 g (54 mmol) of
triethylsilylmethyl propyl sulfide and 0.9 g (54 mmol)
of acetyl iodide was stirred under heating at 70–75°C
for 5 h. Yield 0.7 g (35%), bp 64°C (5 mm Hg), n
1
Voronkov, M.G., Rakhlin, V.I., Mirskov, R.G.,
Khangazheev, S.Kh., Yarosh, O.G., and Tsetlina, E.O.,
Zh. Obshch. Khim., 1979, vol. 49, no. 1, p. 119.
2
0
D
4. Abel, E.W. and Singh, A., J. Chem. Soc., 1959, vol. 2,
–
1
.4780. IR spectrum, ν, cm : 1694 (S–С=О). Found,
: С 54.01; Н 10.46; S 13.51; Si 15.54. С H ОSSi.
p. 690.
%
5. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N.,
9
20
Calculated, %: С 52.94; Н 9.80; S 13.73; Si 15.69. In a
Russ. J. Org. Chem., 2002, vol. 38, no. 11, p. 1579.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 10 2013