JOURNAL OF SULFUR CHEMISTRY
5
1
4
-Chlorostyrene (Table 1, Entry 2): H NMR (300 MHz, CDCl ): δ 7.24–7.34 (m, 4H),
3
1
3
6
.64 (dd, 1H, J = 17.6, 11.1 Hz), 5.71 (d, 1H, J = 17.8 Hz), 5.25 (d, 1H, J = 11.1 Hz). C
+
NMR (75 MHz, CDCl ): δ 136.0, 135.6, 133.4, 128.6, 127.4, 114.4. GC/MS (m/z): 138 (M ),
3
1
40 (M + 2).
1
4
-Bromostyrene (Table 1, Entry 3): H NMR (300 MHz, CDCl ): δ 7.45 (d, 2H,
3
J = 9.6 Hz), 7.23 (d, 2H, J = 9.6 Hz), 6.63 (dd, 1H, J = 17.6, 11.1 Hz), 5.71 (d, 1H,
1
3
J = 17.6 Hz), 5.25 (d, 1H, J = 11.1 Hz). C NMR (75 MHz, CDCl ): δ 136.4, 135.7, 131.6,
3
+
1
27.7, 121.5, 114.5. GC/MS (m/z): 183 (M ), 185 (M + 2).
1
4
-Fluorostyrene (Table 1, Entry 4): H NMR (300 MHz, CDCl ): δ 7.40–7.35 (m, 2H),
3
7
1
.04–6.98 (m, 2H), 6.68 (dd, 1H, J = 17.7, 11.1 Hz), 5.66 (d, 1H, J = 17.7 Hz), 5.22 (d,
1
3
H, J = 10.8 Hz). C NMR (75 MHz, CDCl ): δ 164.1, 135.7, 133.8, 127.8, 115.5, 113.4.
3
+
GC/MS (m/z): 122 (M ).
1
4
-Acetoxystyrene (Table 1, Entry 5): H NMR (300 MHz, CDCl ): δ 7.42 (d, 2H,
3
J = 8.7 Hz), 7.05 (d, 2H, J = 8.7 Hz), 6.71 (dd, 1H, J = 17.4, 11.1 Hz), 5.72 (d, 1H,
1
3
J = 17.4 Hz), 5.25 (d, 1H, J = 11.1 Hz), 2.30 (s, 3H). C NMR (75 MHz, CDCl ): δ 169.3,
3
+
1
6
50.1, 135.8, 135.2, 127.1, 121.6, 113.9, 21.1. GC/MS (m/z): 162 (M ).
1
4
-Allylanisole (Table 1, Entry 6): H NMR (300 MHz, CDCl ): δ 7.08 (d, 2H, J = 8.4 Hz),
3
.82 (d, 2H, J = 8.4 Hz), 5.86–6.00 (m, 1H), 5.01–5.06 (m, 2H), 3.77 (s, 3H), 3.31 (d, 2H,
1
3
J = 6.9 Hz). C NMR (75 MHz, CDCl ): δ 157.9, 137.8, 132.0, 129.4, 115.3, 113.8, 55.2,
3
+
3
9.2. GC/MS (m/z): 148 (M ).
1
Allylphenylether (Table 1, Entry 7): H NMR (300 MHz, CDCl ): δ 7.26–7.33 (m, 2H),
3
6
4
.92–6.99 (m, 3H), 6.04–6.13 (m, 1H), 5.44 (d, 1H, J = 17.9 Hz), 5.30 (d, 1H, J = 12.0 Hz),
1
3
.55 (m, 2H). C NMR (75 MHz, CDCl ): δ 158.6, 133.4, 129.4, 120.8, 117.5, 114.7, 68.7.
3
+
1
Indene (Table 1, Entry 8): H NMR (300 MHz, CDCl ): δ 7.18–7.51 (m, 4H), 6.89–6.92
3
1
3
(
m, 1H), 6.56–6.59 (m, 1H), 3.42 (s, 2H). C NMR (75 MHz, CDCl ): δ 144.7, 143.5, 134.0,
3
+
1
31.9, 126.0, 124.4, 123.6, 120.8, 39.0. GC/MS (m/z): 116 (M ).
1
cis-Stilbene (Table 1, Entry 9): H NMR (300 MHz, CDCl ): δ 7.26–7.67 (m, 10H), 6.61
3
1
3
(
(
s, 2H). C NMR (75 MHz, CDCl ): δ 137.2, 130.2, 128.8, 128.1, 127.0. GC/MS (m/z): 180
M ).
3
+
1
trans-Stilbene (Table 1, Entry 10): H NMR (300 MHz, CDCl ): δ 7.23–7.54 (m, 10H),
.06 (s, 2H). C NMR (75 MHz, CDCl ): δ 137.3, 128.6, 128.5, 127.5, 126.4. GC/MS (m/z):
3
1
3
7
1
3
+
80 (M ).
2
1
-Cyclohexen-1-one (Table 1, Entry 11): H NMR (300 MHz, CDCl ): δ 7.04–7.00 (m,
3
1
H), 6.06–6.01 (m, 1H), 2.45 (t, 2H, J = 6.9 Hz), 2.39–2.33 (m, 2H), 2.07–2.01 (m, 2H).
1
3
+
C NMR (75 MHz, CDCl ): δ 199.6, 150.6, 129.9, 38.2, 25.8, 22.8. GC/MS (m/z): 96 (M ).
3
1
1
-Dodecene (Table 1, Entry 12): H NMR (300 MHz, CDCl ): δ 5.84 (m, 1H), 4.97 (br t,
3
1
3
2
1
H), 2.04 (m, 2H), 1.27 (m, 16H), 0.88 (t, 3H, J = 6.0 Hz). C NMR (75 MHz, CDCl ): δ
3
+
40.1, 115.0, 34.8, 32.9, 30.6, 30.5, 30.3, 30.1, 30.0, 23.7, 15.0. GC/MS (m/z): 168 (M ).
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was financially supported by Korea University Grant.