K. Swapna, S. N. Murthy, Y. V. D. Nageswar
FULL PAPER
Diphenyl Selane (3a):[18f] Yellowish oil (98%, 228 mg; Table 3, En-
(75 MHz, CDCl3): δ = 134.4, 130.2, 129.8, 129.1, 128.0, 127.3,
try 1). 1H NMR (300 MHz, CDCl3): δ = 7.43–7.41 (m, 4 H), 7.31– 118.5, 118.3, 114.0, 113.1 ppm. IR (neat): ν1599, 1576, 1060, 827,
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7.19 (m, 6 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 132.9, 131.1, 730 cm–1. MS (ESI): m/z = 274 [M + Na].
129.2, 127.2 ppm. MS (ESI): m/z = 256 [M + Na].
(4-Chlorophenyl)(phenyl)selane (3k):[23a] Yellowish oil (88%,
234 mg; Table 3, Entry 11). 1H NMR (300 MHz, CDCl3): δ = 7.47–
7.39 (m, 2 H), 7.33 (d, J = 8.0 Hz, 2 H), 7.27–7.19 (m, 5 H) ppm.
13C NMR (75 MHz, CDCl3, TMS): δ = 134.1, 133.3, 129.6,
Phenyl(p-tolyl)selane (3b):[18f] Yellowish oil (90%, 197 mg; Table 3,
Entry 2). 1H NMR (400 MHz, CDCl3): δ = 7.39–7.32 (m, 4 H),
7.24–7.15 (m, 3 H), 7.03 (d, J = 8.49 Hz, 2 H), 2.34 (s, 3 H) ppm.
13C NMR (75 MHz, CDCl3): δ = 137.9, 133.5, 132.3, 130.1, 129.2,
127.5 ppm. IR (neat): ν1595, 1570, 1050 cm–1. MS (ESI): m/z = 290
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[M + Na].
126.9, 21.3 ppm. IR (neat): ν3070, 2858, 1570, 1508, 1055, 915, 842,
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730 cm–1. MS (ESI): m/z = 270 [M + Na].
Phenyl[4-(trifluoromethyl)phenyl]selane (3l):[21a] Yellowish oil (89%,
267 mg; Table 3, Entry 12). 1H NMR (300 MHz, CDCl3): δ = 7.58–
7.50 (m, 2 H), 7.49–7.36 (m, 4 H), 7.35–7.23 (m, 3 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 133.6, 133.4, 132.7, 132.1, 130.2,
Phenyl(o-tolyl)selane (3c):[18f] Yellowish oil (80%, 197 mg; Table 3,
Entry 3). 1H NMR (300 MHz, CDCl3): δ = 7.38–7.31 (m, 2 H),
7.26 (d, J = 7.65 Hz, 1 H), 7.25–7.11 (m, 5 H), 7.01 (t, J = 6.8 Hz,
1 H), 2.32 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 139.9,
133.4, 132.8, 131.9, 130.5, 129.9, 129.3, 127.5, 127.0, 126.5,
129.3, 129.2, 128.4, 127.1, 126.5 ppm. IR (neat): ν1599, 1576, 1060,
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827, 730 cm–1. MS (ESI): m/z = 324 [M + Na].
22.8 ppm. IR (neat): ν3069, 2925, 1575, 1450, 930, 840, 710 cm–1.
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Phenyl[3-(trifluoromethyl)phenyl]selane (3m):[24] Yellowish oil (74%,
222 mg; Table 3, Entry 13). 1H NMR (300 MHz, CDCl3): δ = 7.68–
7.62 (m, 1 H), 7.56–7.41 (m, 4 H), 7.38–7.19 (m, 4 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 135.1, 134.0, 133.2, 129.6, 129.5,
MS (ESI): m/z = 270 [M + Na].
(4-Ethylphenyl)(phenyl)selane (3d):[23a] Yellowish oil (86%, 223 mg;
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Table 3, Entry 4). H NMR (300 MHz, CDCl3): δ = 7.42–7.32 (m,
129.4, 128.4, 128.2, 125.4, 123.6, 121.7 ppm. IR (neat): ν2930, 1577,
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4 H), 7.25–7.16 (m, 3 H), 7.08 (d, J = 8.12 Hz, 2 H), 2.62 (q, J =
7.5, 7.5 Hz, 2 H), 1.24 (t, J = 7.5 Hz, 1 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 139.9, 133.4, 132.8, 131.9, 130.5, 129.9,
1475, 1421, 1320, 1166 cm–1. MS (ESI): m/z = 324 [M + Na].
Phenyl(m-tolyl)selane (3n):[23a] Yellowish oil (80%, 197 mg; Table 3,
Entry 14). 1H NMR (300 MHz, CDCl3): δ = 7.42–7.37 (m, 2 H),
7.28–7.19 (m, 5 H), 7.11 (t, J = 7.5 Hz, 1 H), 7.02 (d, J = 7.5 Hz,
1 H), 2.31 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 139.2,
133.8, 132.7, 131.2, 130.5, 130.2, 129.3, 129.2, 128.4, 127.3,
129.3, 127.5, 127.0, 126.5, 22.8 ppm. IR (neat): ν3054, 2933, 2842,
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1561, 917, 810, 741 cm–1. MS (ESI): m/z = 284 [M + Na].
(3,5-Dimethylphenyl)(phenyl)selane (3e):[22] Yellowish oil (90%,
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234 mg; Table 3, Entry 5). H NMR (400 MHz, CDCl3): δ = 7.41–
21.3 ppm. IR (neat): ν3060, 2925, 2854, 1571, 1508, 1455, 921, 842,
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7.37 (m, 2 H), 7.25–7.17 (m, 3 H), 7.07 (br. s, 2 H), 6.85 (br. s, 1
H), 2.27 (s, 6 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 138.7,
132.4, 131.0, 130.3, 129.2, 129.1, 126.8, 124.3, 21.1 ppm. IR (neat):
717 cm–1. MS (ESI): m/z = 270 [M + Na].
4-(Phenylselanyl)benzaldehyde (3o):[7a] Yellowish oil (85%, 221 mg;
Table 3, Entry 15). 1H NMR (300 MHz, CDCl3): δ = 9.84 (s, 1 H),
7.91–7.31 (m, 4 H), 7.30–7.16 (m, 3 H), 7.09 (d, J = 8.12 Hz, 2
H) ppm. 13C NMR (75 MHz, CDCl3): δ = 192.0, 148.2, 134.2,
ν3050, 2918, 1570, 809, 727 cm–1. MS (ESI): m/z = 284 [M + Na].
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(4-Methoxyphenyl)(phenyl)selane (3f):[18f] Yellowish oil (87%,
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228 mg; Table 3, Entry 6). H NMR (200 MHz, CDCl3): δ = 7.48
133.3, 131.2, 130.1, 129.2, 129.0, 126.9 ppm. IR (neat): ν = 3060,
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(d, J = 8.0 Hz, 2 H), 7.30–7.25 (m, 2 H), 7.23–7.16 (m, 3 H), 6.80
(d, J = 8.0 Hz, 2 H), 3.76 (s, 3 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 159.5, 136.2, 133.5, 131.0, 129.2, 126.5, 119.8, 115.4,
1697, 1597, 1560, 1475, 1403 cm–1. MS (ESI): m/z = 284 [M + Na].
4-(Phenylselanyl)benzonitrile (3p):[25] Yellowish oil (86%, 221 mg;
Table 3, Entry 16). 1H NMR (300 MHz, CDCl3): δ = 7.55–7.49 (m,
4 H), 7.30–7.23 (m, 5 H) ppm. 13C NMR (75 MHz, CDCl3): δ =
55.5 ppm. IR (neat): ν1575, 1490, 1045, 853, 747 cm–1. MS (ESI):
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m/z = 286 [M + Na].
(2-Methoxyphenyl)(phenyl)selane (3g):[23a] Yellowish oil (80%,
210 mg; Table 3, Entry 7). H NMR (300 MHz, CDCl3): δ = 7.45
134.0, 132.9, 129.1, 127.5, 120.2, 116.5 ppm. IR (neat): ν = 2924,
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2250, 1567, 1577, 1403 cm–1. MS (ESI): m/z = 281 [M + Na].
4-(Phenylselanyl)phenol (3q):[18e] Yellowish oil (85%, 211 mg;
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(d, J = 8.5 Hz, 2 H), 7.23–7.18 (m, 5 H), 6.82 (d, J = 8.49 Hz, 2
H), 3.79 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 156.4,
135.3, 130.9, 129.3, 128.5, 128.0, 127.6, 121.9, 121.4, 109.9,
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Table 3, Entry 17). H NMR (300 MHz, CDCl3): δ = 7.44 (d, J =
8.30 Hz, 2 H), 7.34–7.23 (m, 2 H), 7.20–7.11 (m, 3 H), 6.74 (d, J =
8.30 Hz, 2 H), 6.50 (br. s, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ
= 156.1, 136.8, 133.2, 130.5, 129.1, 126.4, 119.8, 116.5 ppm. IR
55.8 ppm. IR (neat): ν = 1577, 1473 cm–1. MS (ESI): m/z = 286 [M
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+ Na].
(neat): ν3400, 1599, 1130 cm–1. MS (ESI): m/z = 272 [M + Na].
(4-tert-Butylphenyl)(phenyl)selane (3h):[23a] Yellowish oil (85%,
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1
1,2-Bis(phenylselanyl)benzene (3r):[16] Yellowish oil (78%, 302 mg;
Table 3, Entry 18). 1H NMR (300 MHz, CDCl3): δ = 7.49–7.32 (m,
6 H), 7.30–7.10 (m, 8 H) ppm. 13C NMR (75 MHz, CDCl3): δ =
133.0, 131.2, 129.2, 128.9, 127.2 ppm. MS (ESI): m/z = 411 [M +
Na].
245 mg; Table 3, Entry 8). H NMR (300 MHz, CDCl3): δ = 7.42–
7.35 (m, 4 H), 7.28–7.19 (m, 5 H), 1.31 (s, 9 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 150.5, 133.2, 132.4, 131.7, 129.1, 127.2,
126.9, 126.4, 34.6, 31.3 ppm. IR (neat): ν3055, 2915, 2854, 1022,
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842, 736 cm–1. MS (ESI): m/z = 312 [M + Na].
(2,4-Dimethoxyphenyl)(phenyl)selane (3i):[23a] Yellowish oil (78%,
228 mg; Table 3, Entry 9). H NMR (200 MHz, CDCl3): δ = 7.41–
1,4-Bis(phenylselanyl)benzene (3s):[23a] White solid; m.p 101–102 °C
1
1
(84%, 325 mg; Table 3, Entry 19). H NMR (300 MHz, CDCl3): δ
= 7.48–7.42 (m, 4 H), 7.29–7.22 (m, 10 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 133.5, 133.2, 130.7, 130.5, 129.4, 127.5 ppm.
MS (ESI): m/z = 411 [M + Na].
7.35 (m, 2 H), 7.26–7.15 (m, 4 H), 6.52–6.40 (m, 2 H), 3.82 (s, 3
H), 3.81 (s, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 161.2,
159.4, 135.6, 132.5, 131.1, 129.1, 126.5, 110.2, 105.5, 98.9, 55.8,
55.3 ppm. IR (neat): ν3058, 2930, 1579, 1061, 917, 827, 735 cm–1.
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(3-Nitrophenyl)(phenyl)selane (3t):[21a] Yellowish oil (70%, 194 mg;
Table 3, Entry 20). 1H NMR (200 MHz, CDCl3): δ = 8.15 (s, 1 H),
MS (ESI): = 317 [M + Na].
(4-Fluorophenyl)(phenyl)selane (3j):[23a] Yellowish oil (89%, 223 mg; 8.03 (d, J = 8.40 Hz, 1 H), 7.61–7.50 (m, 3 H), 7.41–7.24 (m, 4
Table 3, Entry 10). 1H NMR (300 MHz, CDCl3): δ = 7.54–7.51 (m,
H) ppm. 13C NMR (100 MHz, CDCl3): δ = 150.9, 147.8, 137.6,
2 H), 7.41–7.04 (m, 6 H), 6.98–6.85 (m, 1 H) ppm. 13C NMR
133.5, 133.1, 131.9, 129.1, 127.7, 123.5 ppm. IR (neat): ν3040, 3100,
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Eur. J. Org. Chem. 2011, 1940–1946