S.S. Kim et al. / Journal of Organometallic Chemistry 689 (2004) 1734–1738
1737
1
3
4
.1.1. 2-Trimethylsilyloxy-2-phenylpropanenitrile (entry 1)
1
C NMR(CDCl3, 100 MHz): d ¼ 1:30, 30.79, 69.89,
H NMR (CDCl3, 200 MHz): d ¼ 0:17 (s, 9H), 1.86
120.60, 126.82, 128.53, 128.70, 129.47, 130.89, 135.06.
ꢀ
(
s, 3H), 7.36–7.53 (m, 5H).
IR (neat): m(CBN) 2360 cm 1.
1
3
C NMR(CDCl3, 100 MHz): d ¼ 0:89, 33.40, 71.45,
21.43, 124.45, 128.49, 141.86.
HRMS (EI): m=z calcd. for C H NOSi (M ):
1
2
4.1.7. 1-Trimethylsilyloxy-2-cyclohexenecarbonitrile (en-
try 7)
þ
12
17
19.1079. Found: 219.1086.
1
H NMR (CDCl , 200 MHz): d ¼ 0:25 (s, 9H), 1.81–
IR (neat): m(CBN) 2362 cm 1.
ꢀ
3
1
.84 (m, 2H), 2.08–2.13 (m, 4H), 5.77 (m, 1H), 5.94–5.99
(
m, 1H).
13
0
4.1.2. 2-Trimethylsilyloxy-2-(4 -nitrophenyl)phenylpro-
panenitrile (entry 2)
C NMR(CDCl3, 100 MHz): d ¼ 1:40, 18.26, 24.20,
3
6.86, 66.71, 121.75, 127.53, 132.49.
HRMS (EI): m=z calcd. for C10H17NOSi (M ):
95.1079. Found: 195.1073.
1
H NMR (CDCl3, 200 MHz): d ¼ 0:25 (s, 9H), 1.88
þ
(
Hz).
s, 3H), 7.77 (d, 2H, J ¼ 9:2 Hz), 8.30 (d, 2H, J ¼ 9:2
1
ꢀ1
IR (neat): m(CBN) 2355 cm
.
1
3
C NMR(CDCl , 100 MHz): d ¼ 1:07, 29.31, 76.43,
3
1
1
20.98, 124.02, 127.26, 129.89, 142.54.
Anal.calcd. for C12H16N2O3Si: C, 54.52; H, 6.10; N,
4
.1.8. 1-Trimethylsilyloxy-1-indancarbonitrile (entry 8)
1
H NMR (CDCl3, 200 MHz): d ¼ 0:12 (s, 9H), 2.29–
0.60. Found: C, 54.44; H, 6.47; N, 10.50%.
IR (neat): m(CBN) 2360 cmꢀ1.
2.42 (m, 1H), 2.57–2.70(m, 1H), 2.82–3.08 (m, 2 H),
7.24–7.55 (m, 4H).
1
3
C NMR(CDCl3, 100 MHz): d ¼ 1:12, 29.37, 42.79,
0
4.1.3. 2-Trimethylsilyloxy-2-(4 -cholorophenyl)phenyl-
propanenitrile (entry 3)
7
1
6.46, 121.04, 124.08, 125.44, 127.71, 129.94, 142.08,
42.58.
1
H NMR (CDCl , 200 MHz): d ¼ 0:21 (s, 9H), 1.85
3
þ
HRMS (EI): m=z calcd. for C H NOSi (M ):
31.1079. Found: 231.1079.
IR (neat): m(CBN) 2360 cm 1.
1
3
17
(
s, 3H), 7.41–7.48 (m, 4H).
1
2
3
C NMR(CDCl3, 100 MHz): d ¼ 1:00, 33.45, 71.01,
ꢀ
1
5
21.18, 126.04, 128.79, 134.55, 140.68.
Anal.calcd. for C12H16ClNOSi: C, 56.79; H, 6.35; N,
.52. Found: C, 56.86; H, 6.69; N, 5.51%.
4.1.9. 1-Trimethylsilyloxy-1,2,3,4-tetrahydronaphthalene-
1- carbonitrile (entry 9)
IR (neat): m(CBN) 2366 cm 1.
ꢀ
1
H NMR (CDCl3, 200 MHz): d ¼ 0:24 (s, 9H), 1.85–
0
2
7
.41 (m, 4H), 2.83 (t, 2H, 7.00 Hz), 7.07–7.28 (m, 3H),
.60–7.67 (m, 1H).
4.1.4. 2-Trimethylsilyloxy-2-(4 -methoxyphenyl)phenyl-
propanenitrile (entry 4)
1
3
1
C NMR(CDCl , 100 MHz): d ¼ 1:33, 18.69, 28.32,
H NMR (CDCl3, 200 MHz): d ¼ 0:17 (s, 9H), 1.86
3
3
1
7.73, 69.87, 122.11, 126.63, 128.02, 129.06, 129.26,
35.68, 136.11.
IR (neat): m(CBN) 2356 cm 1.
(
s, 3H), 3.84 (s, 3H), 6.95 (d, 2H, J ¼ 8:8 Hz), 7.50 (d,
2
7
2
H, J ¼ 8:8 Hz ).
ꢀ
13
C NMR(CDCl3, 100 MHz): d ¼ 0:98, 33.31, 55.21,
1.18, 113.80, 121.70, 125.96, 133.95, 159.72.
HRMS (EI): m=z calcd. for C H NO Si (M ):
þ
13
19
2
4.1.10.
1-Trimethylsilyloxy-1-cyclohexanecarbonitrile
49.1185. Found: 249.1183.
(
1
3
entry 10)
1
IR (neat): m(CBN) 2362 cm 1.
ꢀ
H NMR (CDCl , 200 MHz): d ¼ 0:23 (s, 9H), 1.51–
3
.68 (m, 8H), 2.02–2.08 (m, 2H).
13
0
4.1.5. 2-Trimethylsilyloxy-3-(4 -methoxyphenyl)-2-meth-
ylphenylpropanenitrile (entry 5)
C NMR(CHCl3, 100 MHz): d ¼ 1:37, 22.59, 24.48,
9.31, 70.59, 121.91.
1
IR (neat): m(CBN) 2352 cm 1.
ꢀ
H NMR (CDCl , 200 MHz): d ¼ 0:15 (s, 9H), 1.51
3
(
2
s, 3H), 2.92(d, 2H, J ¼ 3:4 Hz), 3.80 (s, 3H), 6.88 (d,
H, J ¼ 8:8 Hz), 7.22 (d, 2H, J ¼ 8:4 Hz ).
13
4
1
.1.11. 2-Trimethylsilyloxy-2-methyloctanenitrile (entry
1)
C NMR(CDCl3, 100 MHz): d ¼ 1:06, 28.64, 48.21,
5
5.21, 69.98, 113.57, 121.76, 126.76, 131.66, 158.98.
1
H NMR (CDCl , 200 MHz): d ¼ 0:22 (s, 9H), 0.91
3
IR (neat): m(CBN) 2368 cm 1.
ꢀ
(t, 3H, 6.60 Hz), 1.31–1.74 (m, 8H), 1.57 (s, 3H), 1.68–
1
.74 (m, 2H).
1
3
4.1.6. 2-Trimethylsilyloxy-2-methyl-4-phenyl-3-butenenit-
rile (entry 6)
C NMR(CDCl , 100 MHz): d ¼ 1:15, 13.88, 22.38,
3
24.09, 28.76, 28.84, 31.47, 43.25, 69.56, 121.91.
HRMS (EI): m=z calcd. for C H NOSi (M ):
1
þ
H NMR (CDCl3, 200 MHz): d ¼ 0:27 (s, 9H), 1.77
s, 3H), 6.20 (d, 1H, J ¼ 15:83 Hz), 6.95 (d, 1H, J ¼ 15:8
Hz), 7.34–7.44 (m, 5H ).
1
2
25
(
227.1705. Found: 227.1710.
IR (neat): m(CBN) 2350 cm 1.
ꢀ