2
808
Wang, Li, and Wang
1
38.3, 131.5, 129.0, 128.2, 123.4, 120.2, 89.6, 88.7, 21.4; MS m/z (%) 192
þ
(
M , 100), 165 (15), 139 (4), 115 (6), 94 (10).
[19]
1
H NMR (CDCl ) d 7.50–7.42 (m, 4H), 7.35–7.31 (m, 5H); C NMR
-(4-Bromophenyl)phenylacetylene. MP 83–848C (lit.
82–848C);
13
1
3
(
CDCl ) d 133.0, 131.6, 128.5, 128.4, 122.9, 122.5, 122.2, 90.5, 88.3; MS
3
þ
m/z (%) 258, 256 (M , 97, 100), 176 (88), 151 (37), 128 (17), 88 (61).
[19]
1
-(4-Acetylphenyl)phenylacetylene. MP 95–978C (lit.
95–968C);
1
H NMR (CDCl ) d 7.90 (d, J ¼ 8.40 Hz, 2H), 7.63 (d, J ¼ 8.44 Hz, 2H),
3
1
.53–7.48 (m, 2H), 7.35–7.30 (m, 3H), 2.62 (s, 3H); C NMR (CDCl ) d
3
7
1
2
8
3
97.1, 136.0, 131.7, 131.6, 128.6, 128.4, 128.2, 128.1, 122.7, 92.6, 88.7,
þ
6.5; MS m/z (%) 220 (M , 62), 205 (100), 176 (51), 151 (21), 102 (11),
8 (22).
[
19] 1
1
-(4-Methoxylphenyl)-1-decyne. Oil;
H NMR (CDCl ) d 7.30
3
(
(
(
d, J ¼ 8.72 Hz, 2H), 6.92 (d, J ¼ 8.74 Hz, 2H), 3.74 (s, 3H), 2.38
t, J ¼ 7.01 Hz, 2H), 1.67–1.58 (m, 2H), 1.45–1.29 (m, 10 H), 0.89
1
3
t, J ¼ 6.05 Hz, 3H); C NMR (CDCl ) d 159.1, 132.9, 116.4, 113.9, 88.8,
3
þ
8
0.2, 55.2, 31.8, 29.2, 29.1, 28.9, 22.2, 19.4, 14.1; MS m/z (%) 244 (M ,
1
9), 201 (5), 188 (24), 173 (30), 159 (31), 147 (100), 121 (35), 115 (20), 91
14).
(
1
1
-(4-Acetylphenyl)-1-decyne. Oil; H NMR (CDCl ) d 7.85 (m, 2H),
3
7
.37 (m, 2H), 2.55 (s, 3H), 2.42 (t, J ¼ 7.21 Hz, 2H), 1.61–1.59 (m, 2H),
1
3
1
NMR (CDCl ) d 197.2, 135.7, 131.7, 129.2, 128.2, 94.4, 80.2, 31.9, 29.2,
.44–1.42 (m, 2H), 1.34–1.29 (m, 8H), 0.89 (t, J ¼ 5.21 Hz, 3H);
C
3
2
H, 9.44. Found: C, 84.47; H, 9.36. HRMS (EI) calcd for C H O
9.1, 29.0, 28.6, 26.5, 22.7, 19.6, 14.1. Anal. Calcd for C H O: C, 84.32;
18 24
1
8
24
2
56.1827, found: 256.1836.
-(4-Nitrophenyl)phenylacetylene. MP 120–1218C (lit.
[
19]
1
120–
1
1
228C); H NMR (CDCl ) d 8.20 (d, J ¼ 8.80 Hz, 2H), 7.68 (d, J ¼ 8.76 Hz,
3
1
H), 7.56–7.50 (m, 2H), 7.38–7.34 (m, 3H), 2.60 (s, 3H); C NMR (CDCl )
3
2
d 146.8, 132.2, 131.7, 130.2, 129.2, 128.4, 123.6, 122.0, 94.7, 87.5; MS m/z
3
þ
(
%) 223 (M , 100), 193 (42), 176 (80), 165 (31), 151 (44), 139 (10), 126 (15).
[
21]
1
Diphenylacetylene. MP 59–618C (lit.
d 7.56–7.51 (m, 4H), 7.34–7.30 (m, 6H); C NMR (CDCl ) d 131.5, 128.2,
60–628C); H NMR (CDCl )
3
1
3
3
þ
1
28.1, 123.2, 89.2; MS m/z (%) 178 (M , 100), 152 (20), 126 (9), 89 (15).
[
19]
1
2
CDCl ) d 7.52–7.45 (m, 2H), 7.32–7.22 (m, 5H), 6.99–6.94 (m, 1H);
-Phenylethynylthiophene. 51–538C (lit.
51–538C); H NMR
13
(
C
NMR (CDCl ) d 131.9, 131.5, 128.3, 127.1, 127.0, 123.4, 122.9, 93.1, 82.6;
3
3
þ
MS m/z (%) 184 (M , 100), 152 (20), 139 (20), 92 (10).
[
19] 1
7
-Chloro-1-phenyl-3-hepten-1-yne. Oil;
H NMR (CDCl ) d 7.45–
3
7
1
.41 (m, 2H), 7.32–7.25 (m, 3H), 6.24–6.11 (m, 1H), 5.76 (d, J ¼ 16.90 Hz,
1
3
H), 3.51 (t, J ¼ 6.85 Hz, 2H), 2.36–2.26 (m, 2H), 1.93–1.82 (m, 2H);
C
NMR (CDCl ) d 142.5, 131.5, 128.1, 128.0, 123.3, 111.0, 88.5, 87.8, 44.1,
3