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T. Kusukawa, W. Ando / Journal of Organometallic Chemistry 559 (1998) 11–22
142.41 (s, 2C), 142.54 (s, 1C), 142.67 (s, 1C), 143.06 (s,
1C), 143.24 (s, 1C), 143.53 (s, 1C), 143.60 (s, 1C),
143.75 (s, 2C), 144.36 (s, 2C), 145.09 (s, 1C), 145.55 (s,
1C), 145.66 (s, 1C), 145.72 (s, 1C), 145.92 (s, 1C),
145.96 (s, 2C), 146.08 (s, 1C), 146.14 (s, 1C), 146.15 (s,
2C), 146.21 (s, 2C), 146.39 (s, 2C), 147.08 (s, 1C),
147.24 (s, 1C), 147.30 (s, 1C), 147.37 (s, 1C), 147.83 (s,
1C), 147.86 (s, 1C), 148.68 (s, 1C), 148.73 (s, 1C),
150.51 (s, 1C), 151.63 (s, 1C), 151.69 (s, 1C), 152.30 (s,
1C), 163.49 (s, 1C), 164.57 (s, 1C), 146.80 (s, 1C),
165.55 (s, 1C); FAB-Mass 1218–1220 (M+ +1 cluster).
2h: red brown solid, 1H-NMR (500 MHz, 1:2
CDCl3–CS2) l 0.38 (s, 54H); 13C-NMR (125 MHz, 1:1
CDCl3–CS2) l 2.63 (q), 60.88 (s, 2C), 135.02 (s, 2C),
135.76 (s, 2C), 139.36 (s, 2C), 140.06 (s, 2C), 140.62 (s,
2C), 140.82 (s, 2C), 141.83 (s, 2C), 142.49 (s, 2C),
142.71 (s, 2C), 143.30 (s, 2C), 143.66 (s, 2C), 143.81 (s,
2C), 144.37 (s, 2C), 145.20 (s, 2C), 145.66 (s, 2C),
146.00 (s, 2C), 146.14 (s, 2C), 146.22 (s, 2C), 146.25 (s,
2C), 146.38 (s, 4C), 147.09 (s, 2C), 147.43 (s, 2C),
147.90 (s, 2C), 148.75 (s, 2C), 151.55 (s, 2C), 151.67 (s,
2C), 164.76 (s, 2C), 165.71 (s, 2C); 29Si-NMR (60 MHz,
1:1, CDCl3–CS2) l −52.72, −9.95; FAB-Mass 1215–
1218 (M+ +1 cluster); UV-vis (toluene) umax (nm): 547,
566.
1H), 6.74 (m, 1H), 7.2–7.4 (m, 3H), 7.5–7.6 (m, 2H);
13C-NMR (126 MHz, 1:3 CDCl3–CS2) l=0.20 (q),
0.38 (q), 0.48 (q), 0.56 (q), 31.80 (d), 52.25 (d), 62.96
(s,1C), 77.97 (s,1C), 122.69 (d), 127.99 (d), 128.38 (d),
128.58 (d), 130.92 (s), 132.09 (s,1C), 133.45 (s,1C),
134.32 (s, 1C), 134.52 (s), 135.07 (d), 136.17 (s, 1C),
138.74 (s, 1C), 138.76 (d), 139.44 (s,1C), 140.15 (s, 1C),
140.99 (s,1C), 141.09 (s,1C), 141.37 (s, 1C), 141.45 (s,
1C), 141.50 (s, 1C), 141.53 (s, 1C), 141.55 (s, 1C),
141.64 (s, 1C), 141.66 (s, 1C), 141.74 (s, 1C), 141.78 (s,
1C), 142.22 (s, 1C), 142.30 (s, 1C), 142.59 (s, 1C),
142.81 (s, 2C), 142.90 (s, 1C), 143.35 (s, 1C), 143.41 (s,
1C), 143.45 (s, 1C), 143.90 (s, 1C), 144.11 (s, 1C),
144.24 (s, 1C), 144.41 (s, 1C), 144.47 (s, 1C), 144.80 (s,
1C), 144.99 (s, 1C), 145.02 (s,1C), 145.11 (s, 2C), 145.25
(s, 1C), 145.39 (s, 1C), 145.60 (s, 1C), 145.68 (s, 2C),
145.80 (s, 1C), 145.88 (s, 1C), 145.89 (s, 1C), 145.96 (s,
1C), 146.01 (s, 2C), 146.09 (s, 2C), 146.24 (s, 1C),
146.39 (s, 1C), 147.08 (s, 1C), 147.93 (s, 1C), 155.49 (s,
1C), 158.00 (s, 1C), 159.95 (s, 1C), 160.43 (s, 1C);
FAB-Mass 1223–1226 (M+ +1 cluster); UV-vis
(toluene) umax (nm): 421, 447.
3e: red brown solid; 1H-NMR (500 MHz, 1:1
CDCl3–CS2) l 0.31 (s, 9H), 0.32 (s, 27H), 0.46 (s, 9H),
3.27 (m, 1H), 5.15 (m, 1H), 6.08 (m, 1H), 6.50 (m, 1H),
6.80 (m, 1H); 13C-NMR (126 MHz, 1:1 CDCl3–CS2) l
0.57 (q), 0.99 (q), 1.68 (q), 28.95 (d), 52.4 (d), 63.46 (s,
1C), 78.53 (s, 1C), 122.00 (d), 130.0 (s, ipso), 130.32 (d),
132.40 (s, 1C), 133.66 (s, 1C), 134.60 (s, 1C), 136.27 (s,
1C),138.87 (s, 1C), 139.56 (s, 1C), 140.28 (s, 1C), 140.96
(d), 141.13 (s, 1C), 141.26 (s, 1C), 141.53 (s, 1C), 141.64
(s,1C), 141.68 (s, 2C), 141.73 (s, 1C), 141.82 (s, 1C),
141.88 (s, 1C), 141.93 (s, 1C), 141.95 (s, 1C), 142.38 (s,
1C), 142.46 (s, 1C), 142.53 (s, 1C), 142.79 (s, 1C),
142.98 (s, 1C), 143.10 (s, 1C), 143.50 (s, 1C), 143.56 (s,
1C), 143.64 (s, 1C), 144.07 (s, 1C), 144.30 (s, 1C),
144.42 (s, 1C), 144.59 (s, 1C), 144.77 (s, 1C), 144.95 (s,
1C), 145.16 (s, 1C), 145.21 (s, 1C), 145.26 (s, 1C),
145.29 (s, 1C), 145.42 (s, 1C), 145.50 (s, 1C), 145.85 (s,
2C), 145.91 (s, 1C), 146.00 (s, 1C), 146.07 (s, 2C),
146.13 (s, 1C), 146.18 (s, 1C), 146.20 (s, 1C), 146.26 (s,
1C), 146.28 (s, 1C), 146.43 (s, 1C), 146.73 (s, 1C),
147.27 (s, 1C), 148.19 (s, 1C), 155.88 (s, 1C), 158.23 (s,
1C), 160.27 (s, 1C), 160.74 (s, 1C); 29Si-NMR (80.0
MHz, 1:1 CDCl3–CS2) l −76.87, −19.82, −13.08,
−12.93, −12.39; FAB-Mass 1218–1220 (M+ +1
cluster).
2i: red brown solid, 1H-NMR (500 MHz, 1:1
CDCl3–CS2) l=1.42 (s, 9H), 1.45 (s, 9H), 2.34 (s, 9H),
2.36 (s, 9H), 7.12 (d, 2H, J=7.6 Hz), 7.16 (d, 2H,
J=7.6 Hz), 7.3–7.5 (m, 6H), 7.82 (d, 2H, J=7.8 Hz),
7.88 (d, 2H, J=7.8 Hz), 7.94 (d, 2H, J=7.6 Hz), 8.01
(d, 2H, J=7.6 Hz); 13C-NMR (126 MHz, 1:1 CDCl3–
CS2) l=21.60 (q), 21.62 (q), 22.26 (s), 22.37 (s), 29.11
(q), 29.18 (q), 64.52 (s, 1C), 65.06 (s, 1C), 127.42 (d),
127.53 (d), 127.57 (s, two carbons), 128.26 (d), 128.37
(d), 129.96 (d), 130.03 (d), 131.21 (s), 131.17 (s), 136.56
(s, 1C), 136.57 (s, 2C), 136.68 (s, 1C), 137.34 (d), 137.40
(d), 137.48 (d), 137.54 (d), 138.65 (s, 1C), 138.73 (s, 1C),
139.41 (s, 1C), 139.67 (s, 1C), 139.74 (s, 1C), 139.80 (s,
1C), 140.57 (s, 1C), 140.58 (s, 1C), 141.29 (s, 1C),
141.33 (s, 1C), 141.48 (s, 1C), 141.50 (s, 1C), 142.07 (s,
2C), 142.19 (s, 1C), 142.33 (s, 1C), 142.39 (s, 1C),
143.38 (s, 2C), 143.79 (s, 1C), 143.82 (s, 1C), 144.32 (s,
1C), 144.36 (s, 1C), 145.44 (s, 1C), 145.46 (s, 1C),
145.80 (s, 1C), 145.84 (s, 1C), 145.86 (s, 2C), 145.90 (s,
2C), 146.02 (s, 2C), 146.06 (s, 1C), 146.09 (s, 1C),
146.36 (s, 1C), 146.39 (s, 1C), 146.75 (s, 1C), 146.83 (s,
1C), 146.91 (s, 1C), 146.92 (s, 1C), 146.96 (s, 1C),
147.02 (s, 1C), 147.73 (s, 1C), 147.77 (s, 1C), 148.55 (s,
1C), 148.57 (s, 1C), 149.77 (s, 1C), 150.56 (s, 1C),
152.85 (s, 1C), 162.06 (s, 1C), 162.27 (s, 1C), 163.79 (s,
1C), 164.06 (s, 1C); 29Si-NMR (80 MHz, 1:1 CDCl3–
CS2) l= −3.67, −4.07; FAB-Mass 1227–1230 (M+
+1 cluster).
1
3f: brown solid, H-NMR (500 MHz, 1:1 CDCl3–
CS2) l 0.09 (s, 9H), 0.42 (s, 9H), 3.62 (s, 1H), 5.25 (s,
1H), 6.21 (m,1H), 6.69 (m, 1H), 6.74 (m, 1H), 7.3–7.4
(m, 3H), 7.62 (d, 2H, J=6.2 Hz); 13C-NMR (126 MHz,
1:1 CDCl3–CS2) l 0.10 (q), 0.31 (q), 31.90 (d), 53.38
(d), 63.47 (s, 1C), 78.07 (s, 1C), 127.95 (d), 129.83 (d),
132.41 (s, 1C), 132.84 (s), 133.32 (s, 1C), 133.65 (s),
134.19 (s, 1C),136.01 (d), 136.59 (s, 1C), 138.90 (s, 1C),
139.50 (s, 1C), 140.40 (s, 1C), 141.09 (s, 1C), 141.21 (s,
1
3d: brown solid, H-NMR (500 MHz, 1:3 CDCl3–
CS2) l=0.27 (s, 9H), 0.30 (s, 9H), 0.36 (s, 9H), 0.40 (s,
9H), 3.45 (m, 1H), 5.11 (m, 1H), 6.11 (m, 1H), 6.56 (m,