1-Heteroakylation of Tris(trimethylsilyl)phosphine 445
TABLE 2 Element Analyses Data of Compounds
Calcd (%)
Found (%)
C
No.
Empirical Formula
C H N P
Formula Weight
C
H
H
2
3
4
5
6
7
8
9
205.28
289.44
373.60
457.76
325.46
263.47
275.48
166.16
208.24
250.32
292.40
236.44
208.11
248.34
340.62
161.26
201.32
52.66
62.25
67.51
70.84
66.43
45.59
47.96
43.37
51.91
57.58
61.62
40.64
34.63
48.37
42.31
44.69
53.69
11.78
12.53
12.95
13.21
11.15
9.95
9.51
9.10
10.17
10.87
11.38
8.95
4.36
8.52
9.76
10.00
10.01
52.49
11.64
12.40
12.81
13.03
11.01
9.74
9.26
8.95
10.02
10.68
11.12
8.89
9
24 3
C15H36N P
61.97
67.26
70.68
66.29
45.21
47.73
43.01
51.72
57.30
61.49
40.29
34.37
48.15
42.12
44.48
53.52
3
C21H48N P
3
C27H60N P
3
C18H36N P
3
C10H26NOPSi2
C11H26NOPSi2
C H O P
6
15
3
1
1
1
1
1
1
1
1
1
0
1
2
3
4
5
6
7
8
C H O P
9
21
3
C12H27O P
3
C15H33O P
3
C H O PSi
8
21
2
2
C H O P
4.20
8.45
9.65
9.81
6
9
6
C10H21O PSi
3
C12H33O PSi3
3
C H16NPSi
6
C H20NPSi
9
9.83
for 1 h, and then the solvent was distilled off under
heating to 90 C. The residue was distilled in a
vacuum to give 8.8 g of phosphine 16.
C-Dimethylamino-P-trimethylsilylphosphaethyle-
ne (17). To a solution of 6.1 g of phosphine 1 in
[9] Mironova, Z. N.; Tsvetkov, E. N.; Petrovskaya, L.
I.; Negrebetsky, V. V.; Nikolaev, A. V.; Kabachnik,
M. I. Zh Obshch Khim 1972, 42, 2152–2158 (in
Russian).
10] Shumann, H.; Roesch, L. Chem Ber 1974, 107, 854–
868.
◦
[
3
0 mL of tetrahydrofuran, 28 mL of 1 M solution
[11] Boehme, H.; Koch, L.; Koehler, E. Chem Ber 1962,
5, 1849–1858.
[12] Prishchenko, A. A.; Livantsov, M. V.; Novikova,
O. P.; Livantsova, L. I.; Petrosyan, V. S. Heteroat
Chem 2008, 19, 418–428.
[13] Prishchenko, A. A.; Livantsov, M. V.; Novikova,
O. P.; Livantsova, L. I.; Petrosyan, V. S. Heteroat
Chem 2009, 20, 319–324.
9
of butyllithium in hexane was added dropwise
under cooling at –30 C and stirring. The mixture
was stirred under –20 C for 4 h and was left for
◦
◦
12 h, and then 3.6 g of dimethylformamide was
added. The mixture was left for 5 h, 5.3 g of
chlorotrimethylsilane was added, and then the
mixture was left for 24 h. The solvent was removed,
and 150 mL of pentane was added. The precipitate
was removed, the solvent was distilled off in a
vacuum, and the residue was distilled to give 2.5 g of
[14] Aguiar, A. M.; Hansen, K. C.; Mague, G. T. J Org
Chem 1967, 32, 2383–2387.
[
15] Frank, A. W.; Drake, G. L. J Org Chem 1971, 36, 3461–
3464.
[16] Becker, G. Z Anorg Allg Chem 1976, 423, 242–
54.
2
phosphaethylene 17.
[
[
17] Becker, G. Z Anorg Allg Chem 1977, 430, 66–76.
18] Kozlov, E. S.; Tovstenko, V. I.; Markovsky, L. N. Zh
Obshch Khim 1977, 47, 954 (in Russian).
Phosphaethylene 18 was prepared similarly.
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[
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[
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[
[
[
[
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[
[
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25] Regitz, M. Methoden der Organischen Chemie
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(
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Heteroatom Chemistry DOI 10.1002/hc