E
E. Buxaderas et al.
Paper
Synthesis
following known compounds included in Table 2 were characterized
by comparison of their chromatographic and spectroscopic data (FT-
IR, 1H NMR, 13C NMR, and MS) with those described in the literature.
1H NMR (300 MHz, CDCl3): δ = 8.57 (d, J = 4.8 Hz, 1 H), 7.64 (dt, J = 8.0,
2.0 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.17–7.13 (m, 1 H), 6.82 (dd, J =
17.6, 10.8 Hz, 1 H), 6.20 (dd, J = 17.6, 1.2 Hz, 1 H), 5.48 (dd, J = 10.8, 1.2
Hz, 1 H).
Styrene (2a)18
13C NMR (75 MHz, CDCl3): δ = 155.6, 149.4, 136.8, 136.5, 122.4, 121.2,
118.2.
Yield: 46 mg (0.44 mmol, 89%); colorless liquid.
MS: m/z (%) = 105 (100, [M+]), 105 (55), 79 (80), 78 (16), 52 (22), 51
IR (film): 3082, 3060, 3027, 1630, 1496, 1449, 992, 909, 777, 698 cm–1
.
(20), 50 (11).
1H NMR (300 MHz, CDCl3): δ = 7.35 (m, 2 H), 7.25 (m, 3 H), 6.7 (dd, J =
10.8, 17.1 Hz, 1 H), 5.71 (d, J = 17.1 Hz, 1 H), 5.20 (d, J = 10.8 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 137.5, 128.5, 127.7, 126.1, 136.9, 113.7.
MS: m/z (%) = 104 (100, [M+]), 103 (40), 78 (35), 77 (17), 51 (17).
2-Methoxy-6-vinylnaphthalene (2f)22
Yield: 50 mg (0.29 mmol, 58%); pale yellow solid; mp 93–95 °C.
IR (KBr): 3054, 2838, 1633, 1597, 1482, 1258 cm–1
.
1H NMR (300 MHz, CDCl3): δ = 7.72–7.68 (m, 3 H), 7.62 (d, J = 8.5 Hz, 1
H), 7.14 (d, J = 8.13 Hz, 2 H), 6.89 (dd, J = 17.6, 10.9 Hz, 1 H), 5.85 (d, J =
17.6 Hz, 1 H), 5.29 (d, J = 10.9 Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 157.7, 136.9, 134.2, 132.9, 129.5, 128.8,
126.9, 126.1, 123.7, 118.9, 113.0, 105.7, 55.2.
1-Methyl-4-vinylbenzene (2b)19
Yield: 50 mg (0.43 mmol, 85%); colorless liquid.
IR (KBr): 3007, 1629, 1511, 1403, 990, 904, 824, 730 cm–1
1H NMR (300 MHz, CDCl3): δ = 7.35 (d, J = 8.0 Hz, 2 H), 7.18 (d, J = 8.0
Hz, 2 H), 6.74 (dd, J = 17.7, 10.7 Hz, 1 H), 5.74 (d, J = 17.5 Hz, 1 H), 5.23
(d, J = 10.9 Hz, 1 H), 2.39 (s, 3 H).
.
MS: m/z (%) = 184 (100, [M+]), 169 (17), 141 (50), 115 (19).
13C NMR (75 MHz, CDCl3): δ = 137.5, 136.6, 134.8, 129.1, 126.0, 112.7,
21.1.
MS: m/z (%) = 118 (100, [M+]), 117 (90), 115 (23), 91 (26).
1-Octene (2g)23
Yield: 52 mg (0.46 mmol, 93%); colorless liquid.
IR (film): 2959, 2928, 2857, 910 cm–1
.
1H NMR (300 MHz, CDCl3): δ = 5.76–5.86 (m, 1 H), 4.90–5.20 (m, 2 H),
2.04 (dd, J = 14.8, 6.4 Hz, 2 H), 1.21–1.46 (m, 8 H), 0.87 (t, J = 8.0 Hz, 3
H).
13C NMR (75 MHz, CDCl3): δ = 138.5, 115.4, 114.0, 33.8, 31.7, 28.6,
22.6, 14.0.
MS: m/z (%) = 112 (20, [M+]), 84 (22), 83 (34), 71 (12), 70 (86), 69 (44),
57 (19), 56 (87), 55 (99), 43 (100), 42 (66), 41 (82), 39 (28), 29 (35), 27
(25).
1-Chloro-3-vinylbenzene (2c)19
Yield: 64 mg (0.47 mmol, 94%); pale yellow liquid.
IR (KBr): 3063, 1594, 1564, 1474, 1414, 1396, 1202, 966, 914, 881,
847, 840, 788, 710, 685, 649 cm–1
.
1H NMR (300 MHz, CDCl3): δ = 7.40 (s, 1 H), 7.20–7.31 (m, 3 H), 6.66
(dd, J = 17.5, 10.9 Hz, 1 H), 5.76 (d, J = 17.5 Hz, 1 H), 5.31 (d, J = 10.9
Hz, 1 H).
13C NMR (75 MHz, CDCl3): δ = 115.3, 124.2, 126.1, 127.7, 129.7, 134.4,
135.5, 139.3.
1-Vinylcyclohexene (2h)24
Yield: 47 mg (0.43 mmol, 87%); colorless liquid.
MS: m/z (%) = 140 (32, [M+ + 2]), 139 (10, [M+ + 1]), 138 (100, [M+]),
IR (neat): 3088, 3003, 2926, 2859, 2835, 1641, 1605, 1449, 1436,
1349, 1314, 1269, 1186, 1136, 1080, 1024, 988, 916, 890, 845, 802
103 (75), 102 (16), 77 (25), 75 (11), 51 (22), 50 (11).
cm–1
.
1-(Trifluoromethyl)-2-vinylbenzene (2d)20
1H NMR (300 MHz, CDCl3): δ = 6.34 (dd, J = 17.52, 28.19 Hz, 1 H), 5.76
(s, 1 H), 5.06 (d, J = 17.69 Hz, 1 H), 4.88 (d, J = 10.8 Hz, 1 H), 2.09–2.18
(m, 4 H), 1.55–1.73 (m, 4 H).
13C NMR (75 MHz, CDCl3): δ = 140.4 136.2, 130.0, 109.7, 25.9, 23.9,
22.7, 22.5.
Yield: 77 mg (0.45 mmol, 90%); colorless liquid.
IR (film): 3010, 1670, 1486, 1310, 1180, 1156, 1124, 1070, 1028, 976,
770, 695 cm–1
.
1H NMR (300 MHz, CDCl3): δ = 7.66 (d, J = 7.8 Hz, 1 H), 7.63 (d, J = 7.8
Hz, 1 H), 7.52 (t, J = 7.6 Hz, 1 H), 7.36 (t, J = 7.7 Hz, 1 H), 7.10 (ddd, J =
17.3, 11.0, 2.5 Hz, 1 H), 5.75 (d, J = 17.1 Hz, 1 H), 5.42 (dd, J = 11.0, 1.2
Hz, 1 H).
MS: m/z (%) = 108 (33, [M+]), 93 (64), 91 (29), 80 (21), 79 (100), 78
(14), 77 (35), 67 (14), 65 (13), 51 (15), 41 (17), 39 (26).
13C NMR (75 MHz, CDCl3): δ = 137.0, 133.3, 132.1, 127.7, 127.3, 125.8
(q), 125.6, 123.4, 118.2.
1-(4-Vinylphenyl)ethan-1-one (2i)25
Yield: 68.6 mg (0.47 mmol, 94%); colorless oil.
MS: m/z (%) = 172 (83, [M+]), 171 (48), 153 (22), 152 (38), 151 (100),
133 (33), 127 (12), 126 (10), 125 (13), 122 (25), 103 (26), 102 (12),
101 (13), 77 (16), 76 (10), 75 (26), 74 (19), 69 (15), 63 (13), 51 (22), 50
(22).
IR (film): 3029, 2926, 1683, 1611, 1456, 1377, 1366, 1265, 954, 827
cm–1
.
1H NMR (300 MHz, CDCl3): δ = 7.93 (d, J = 8.4 Hz, 2 H), 7.49 (d, J = 8.2
Hz, 2 H), 6.76 (dd, J = 17.6, 10.9 Hz, 1 H), 5.90 (d, J = 17.6 Hz, 1 H), 5.41
(d, J = 10.9 Hz, 1 H), 2.59 (s, 3 H).
2-Vinylpyridine (2e)21
13C NMR (75 MHz, CDCl3): δ = 197.7, 142.2, 136.4, 136.0, 128.8, 128.6,
Yield: 46 mg (0.44 mmol, 87%); colorless liquid.
IR (film): 3016, 1588, 1564, 1474, 1435, 989, 802, 746 cm–1
.
126.4, 116.8, 26.7.
MS: m/z (%) = 146 (42, [M+]), 131 (100), 103 (64).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–G