118
S. Langle et al. / Journal of Organometallic Chemistry 671 (2003) 113ꢀ119
/
(70 eV) m/z: 348 [Mꢁ&z.rad, 2], 291 (100), 235 (87), 179
(62), 151 (12).
1.2.7. 4-Tributylstannylmethylstyrene (2k) [24,28]
1H-NMR d ppm (CDCl3, 200 MHz): 0.88ꢀ
1.00 (15H,
m), 1.31ꢀ1.58 (12H, m), 2.40 (2H, s, JSnÃH 57 Hz),
5.17 (1H, d, Jꢂ10.9 Hz), 5.71 (1H, d, Jꢂ17.6 Hz), 6.72
(1H, dd, Jꢂ17.6 Hz, Jꢂ10.9 Hz), 7.03 (2Har, d, Jꢂ8.2
Hz), 7.30 (2Har, d, Jꢂ
8.2 Hz); 13C-NMR d ppm
(CDCl3, 50 MHz): 9.8 (3C, JSnÃC 318ꢀ303 Hz), 14.1
(3C), 22.5, 28.0 (3C, JSnÃC 55ꢀ52 Hz), 29.6 (3C,
/
/
ꢂ
/
/
/
1.2.3. 4-Tributylstannylstyrene (2e) [27]
IR: 2958, 2926, 1629, 1461, 1386, 907, 821; H-NMR
/
/
/
1
/
d ppm (CDCl3, 200 MHz): 0.87ꢀ
1.12 (6H, m), 1.29ꢀ1.40 (6H, m), 1.52ꢀ
5.23 (1H, d, Jꢂ10.9 Hz), 5.78 (1H, d, Jꢂ
(1H, dd, Jꢂ17.6 Hz, Jꢂ10.9 Hz), 7.36 (2Har, d, Jꢂ
Hz), 7.45 (2Har, d, Jꢂ
8.1 Hz); 13C-NMR d ppm
(CDCl3, 50 MHz): 9.9 (3C, JSnÃC 340ꢀ326 Hz), 13.9
(3C), 27.8 (3C, JSnÃC 57ꢀ55 Hz), 29.5 (3C, JSnÃC
20.2 Hz), 113.7, 125.9 (2C, JSnÃC 42ꢀ40 Hz), 137.1
368
/
0.94 (9H, m), 1.04ꢀ
1.61 (6H, m),
17.6 Hz), 6.71
8.1
/
ꢂ
/
/
/
/
ꢂ
/
/
/
/
JSnÃC
ꢂ20 Hz), 111.6, 126.7 (2C), 127.6 (2C), 133,
/
/
/
/
137.4, 145.0; MS (70 eV) m/z: 408 [Mꢁ&z.rad, 6], 351
/
(5), 291 (76), 235 (100), 179 (85), 117 (84); 119Sn-NMR
ꢂ
/
/
(CDCl3, 74.2 Hz) d ppm: ꢃ3.4.
/
ꢂ
/
/
ꢂ
/
ꢂ
/
/
1.2.8. 4-Di(dimethylgermylmethyl)styrene (2l)
1H-NMR d ppm (CDCl3, 200 MHz): 0.05 (6H, s),
(2C, JSnÃC
ꢂ
/
30 Hz), 137.4, 137.6, 142.4 (JSnÃC
ꢂ
/
38ꢀ
/
Hz); MS (70 eV) m/z: 394 [Mꢁ&z.rad, 1], 337 (81), 281
2.25 (4H, s), 5.16 (2H, d, Jꢂ
17.6 Hz), 6.69 (2H, dd, Jꢂ10.9 Hz, Jꢂ
(4H, d, Jꢂ8.17 Hz), 7.28 (4H, d, Jꢂ
8.17 Hz); 13C-
NMR d ppm (CDCl3, 50 MHz): ꢃ4.4 (2C), 24.8 (2C),
/
10.9 Hz), 5.68 (2H, d, Jꢂ
/
(52), 223 (100), 197 (12), 121 (12).
/
/17.6 Hz), 6.96
/
/
1.2.4. 4-Tributylsilylmethylstyrene (2g)
/
1H-NMR d ppm (CDCl3, 200 MHz): 0.87ꢀ
/
1.35 (27H,
10.9 Hz), 5.69 (1H, d,
17.6 Hz, Jꢂ10.9 Hz),
8.2 Hz), 7.29 (2Har, d, Jꢂ8.2 Hz);
112.1 (2C), 126.4 (4C), 128.3 (4C), 133.8 (2C), 137.1
(2C), 141.2 (2C); MS (70 eV) m/z: 338 [Mꢁ&z.rad, 55],
221 (100), 117 (88), 91 (15).
m), 2.13 (2H, s), 5.16 (1H, d, Jꢂ
Jꢂ17.6 Hz), 6.70 (1H, dd, Jꢂ
7.00 (2Har, d, Jꢂ
/
/
/
/
/
/
13C-NMR d ppm (CDCl3, 50 MHz): 12.1 (3C), 14.0
(3C), 26.4 (3C), 27.2 (3C or 1C), 27.3 (3C or 1C), 112.0,
126.4 (2C), 128.7 (2C), 133.7, 137.3, 141.3; MS (70 eV)
m/z: 316 [Mꢁ&z.rad, 10], 199 (84), 143 (100), 101 (17),
87 (13), 59 (10). Anal. Calc. for C21H36Si: C, 79.67; H,
11.46. Found: C, 79.65; H, 11.41%.
1.2.9. 1-Bromo-3-p-styrylpropane (3)
1H-NMR d ppm (CDCl3, 200 MHz): 2.15 (2H, m,
Jꢂ
Hz), 5.21 (1H, d, Jꢂ
6.71 (1H, dd, Jꢂ10.9 Hz, Jꢂ
Jꢂ8.1 Hz), 7.36 (2Har, d, Jꢂ
8.1 Hz); 13C-NMR d ppm
/
6.8 Hz), 2.76 (2H, t, Jꢂ
10.9 Hz), 5.73 (1H, d, Jꢂ
17.6 Hz), 7.17 (2Har, d,
/
6.8 Hz), 3.41 (2H, t, Jꢂ
/
6.8
/
/
17.6 Hz),
/
/
/
/
(CDCl3, 50 MHz): 33.6, 34.0, 34.5, 113.3, 126.5 (2C),
129.0 (2C), 140.2, 140.8, 144.8.
1.2.5. 4-Triethylgermylmethylstyrene (2i)
IR: 3015, 2949, 2904, 2870, 1628, 1509, 840; 1H-NMR
1.2.10. 1-Trimethylsilyl-3-p-styrylpropane (4a)
IR: 3100, 3015, 1640, 1520, 1420, 1260, 1000; 1H-
NMR d ppm (CDCl3, 200 MHz): 0.09 (9H, s), 0.64 (2H,
d ppm (CDCl3, 200 MHz): 0.70ꢀ
Hz), 0.96ꢀ1.04 (9H, t, Jꢂ7.1 Hz), 2.23 (2H, s), 5.13
(1H, d, Jꢂ10.9 Hz), 5.66 (1H, d, Jꢂ17.6 Hz), 6.67 (1H,
dd, Jꢂ17.6 Hz, Jꢂ10.9 Hz), 6.98 (2Har, d, Jꢂ8.1 Hz),
7.26 (2Har, d, Jꢂ
8.1 Hz); 13C-NMR d ppm (CDCl3, 50
/
0.78 (6H, q, Jꢂ
/7.1
/
/
/
/
m), 1.71 (2H, m), 2.71 (2H, t, Jꢂ
Jꢂ10.9 Hz, Jꢂ1 Hz), 5.81 (1H, dd, Jꢂ
Hz), 6.80 (1H, dd, Jꢂ17.6 Hz, Jꢂ10.9 Hz), 7.24 (2Har,
d, Jꢂ8.1 Hz), 7.44 (2Har, d, Jꢂ
8.1 Hz); 13C-NMR d
ppm (CDCl3, 50 MHz): ꢃ1.7 (3C), 16.5 (JSiÃC 51 Hz),
/7.5 Hz), 5.29 (1H, dd,
/
/
/
/
/
/
17.6 Hz, Jꢂ1
/
/
/
/
MHz): 4.1 (3C), 8.9 (3C), 21.1, 111.9, 126.4 (2C), 128.2
(2C), 133.4, 137.2, 141.9; MS (70 eV) m/z: 278
[Mꢁ&z.rad, 90], 249 (18), 219 (11), 191 (14), 161
(100), 133 (68), 117 (38), 103 (18). Anal. Calc. for
C15H24Ge: C, 65.05; H, 8.73. Found: C, 65.15; H,
8.67%.
/
/
/
ꢂ
/
26.0, 39.6, 112.7, 126.1 (2C), 128.6 (2C), 135.0, 136.7,
142.4; MS (70 eV) m/z: 218 [Mꢁ&z.rad, 6], 101 (10), 73
(100), 59 (13), 45 (12); 29Si-NMR d ppm: 1.42, JSiÃH
6.5 Hz. Anal. Calc. for C14H22Si: C, 76.99; H, 10.15.
Found: C, 77.05; H, 9.89%.
ꢂ
/
1.2.6. 4-Tributylgermylmethylstyrene (2j)
IR: 2956, 2924, 2870, 2855, 1629, 1464, 1376, 899,
1.2.11. 1-Trimethylgermyl-3-p-styrylpropane (4b)
1H-NMR d ppm (CDCl3, 200 MHz): 0.16 (9H, s),
1
839; H-NMR d ppm (CDCl3, 200 MHz): 0.70ꢀ
/
1.36
10.9 Hz), 5.68
17.6 Hz, Jꢂ10.9
8.2 Hz), 7.26 (2Har, d, Jꢂ8.2
(27H, m), 2.24 (2H, s), 5.14 (1H, d, Jꢂ
(1H, d, Jꢂ17.6 Hz), 6.69 (1H, dd, Jꢂ
Hz), 6.99 (2Har, d, Jꢂ
/
0.78ꢀ
5.22 (1H, dd, Jꢂ
17.6 Hz, Jꢂ1 Hz), 6.74 (1H, dd, Jꢂ
Hz), 7.18 (2Har, d, Jꢂ8.2 Hz), 7.37 (2Har, d, Jꢂ
Hz); 13C-NMR d ppm (CDCl3, 50 MHz): ꢃ
2.3 (3C),
/
1.00 (2H, m), 1.65ꢀ
/
1.75 (2H, m), 2.64 (2H, t, J),
1 Hz), 5.74 (1H, dd, Jꢂ
17.6 Hz, Jꢂ10.9
8.2
/
/
/
/
10.9 Hz, Jꢂ
/
/
/
/
/
/
/
Hz); 13C-NMR d ppm (CDCl3, 50 MHz): 12.8 (3C),
14.1 (3C), 22.5, 27.2 (3C), 27.9 (3C), 111.9, 126.6 (2C),
128.5 (2C), 133.7, 137.4, 145.0; MS (70 eV) m/z: 362
[Mꢁ&z.rad, 30], 245 (82), 189 (100), 165 (13), 133 (25),
117 (22), 91 (6).
/
/
/
16.9, 27.6, 39.7, 112.9, 126.4 (2C), 129.0 (2C), 135.4,
137.1, 143.0; MS (70 eV) m/z: 264 [Mꢁ&z.rad, 12], 249
(84), 236 (28), 119 (100), 105 (26), 91 (13).