ORDER
REPRINTS
CATALYZED OLEFINATION OF ALDEHYDES
199
1
3
7
1
.79 (d, 1H, J ¼ 16.1 Hz), 11.31 (b, 1H); C NMR (CDCl ): d 117.51, 128.44,
3
29.03, 130.78, 134.20, 147.15, 172.68.
(
2E )-3-(4-Methylphenyl)prop-2-enoic Acid(2b):
Colorless crystals.
198–199 C); IR (KBr): 3250–2350,
H NMR (CDCl ): d 2.38 (s, 3H), 6.40 (d, 1H,
ꢀ
24b
ꢀ
Yield: 70%; m.p.: 197–198 C (lit.
684, 1624 cm
ꢂ1
1
1
;
3
J ¼ 16.1 Hz), 7.20 (d, 2H, J ¼ 7.9 Hz), 7.45 (d, 2H, J ¼ 7.9 Hz), 7.76 (d, 1H,
1
3
J ¼ 16.1 Hz); C NMR (CDCl ): d 21.57, 116.32, 128.47, 129.79, 131.53,
3
1
41.34, 147.15, 172.44.
(
7%; m.p.: 154–158 C (lit. (C-N) 152.4 C, (N-I) 157.6 C); IR (KBr): 3350–
2E )-3-(4-Ethylphenyl)prop-2-enoic Acid(2c): Colorless crystals. Yield:
ꢀ ꢀ ꢀ
22
6
2
2
2
ꢂ1
1
360, 1684, 1628 cm ; H NMR (CDCl ): d 1.24 (t, 3H, J ¼ 7.5 Hz), 2.68 (q,
3
H, J ¼ 7.5 Hz), 6.40 (d, 1H, J ¼ 15.8 Hz), 7.23 (d, 2H, J ¼ 8.4 Hz), 7.47 (d,
1
3
H, J ¼ 8.4 Hz), 7.76 (d, 1H, J ¼ 15.8 Hz), 10.09 (b, 1H); C NMR (CDCl ):
3
d 15.27, 28.88, 116.39, 128.54, 131.69, 147.15, 147.58, 172.91.
2E )-3-(4-Isopropylphenyl)prop-2-enoic Acid(2 )d : Colorless crystals.
Yield: 71%; m.p.: 160–162 C (lit. 159–160 C): IR (KBr): 3350–2350,
(
ꢀ
25
ꢀ
ꢂ1
1
1
1
684, 1624 cm ; H NMR (CDCl ): d 1.23 (d, 6H, J ¼ 6.8 Hz), 2.91 (sept.
3
H, J ¼ 6.8 Hz), 6.38 (d, 1H, J ¼ 16.1 Hz), 7.23 (d, 2H, J ¼ 8.1 Hz), 7.46
1
3
(
d, 2H, J ¼ 8.1 Hz), 7.74 (d, 1H, J ¼ 16.1 Hz) 10.25 (b, 1H); C NMR (CDCl ):
3
d 23.76, 34.17, 116.46, 127.13, 128.57, 131.84, 147.13, 152.17, 172.93.
2E )-3-(4-Chlorophenyl)prop-2-enoic Acid(2e): Colorless crystals.
Yield: 73%; m.p.: 247–249 C (lit. 248–249 C); IR (KBr): 3250–2325,
(
ꢀ
25
ꢀ
ꢂ1
1
1
684, 1626 cm ; H NMR (DMSO-d ): d 6.51 (d, 1H, J ¼ 16.0 Hz), 7.45
6
(
d, 2H, J ¼ 8.5 Hz), 7.56 (d, 1H, J ¼ 16.0 Hz), 7.69 (d, 2H, J ¼ 8.5 Hz),
1
3
1
2.48 (b, 1H); C NMR (DMSO-d ): d 120.35, 129.24, 130.11, 133.48,
6
135.12, 142.83, 167.78.
(
2E )-3-(2-Methylphenyl)prop-2-enoic Acid(2f ):
Colorless crystals.
174–176 C); IR (KBr): 3250–2350,
H NMR (CDCl ): d 2.46 (s, 3H), 6.38 (d, 1H,
ꢀ
26a
ꢀ
Yield: 70%; m.p.: 177–178 C (lit.
684, 1622 cm
ꢂ1
1
1
;
3
J ¼ 15.6 Hz), 7.15–7.38 (m, 3H), 7.52–7.65 (m, 1H), 8.09 (d, 1H,
1
3
J ¼ 15.6 Hz); C NMR (CDCl ): d 19.79, 118.36, 126.51, 126.78, 130.52,
3
1
30.97, 133.17, 138.01, 144.80, 172.03.
(
2E )-3-(4-Methoxyphenyl)prop-2-enoic Acid(2g): Colorless crystals.
ꢀ
26b
ꢀ ꢀ
170–173 C) and {(C-N) 170 C, (N-I)
Yield: 68%; m.p.: 168–170 C (lit.
ꢀ
23
ꢂ1
1
1
82 C} ; IR (KBr): 3225–2350, 1685, 1624 cm ; H NMR (CDCl ): d 3.84
3
(
s, 3H), 6.30 (d, 1H, J ¼ 15.8 Hz), 6.91 (d, 2H, J ¼ 8.7 Hz), 7.49 (d, 2H,
1
3
J ¼ 8.7 Hz), 7.73 (d, 1H, J ¼ 15.8 Hz); C NMR (CDCl ): d 55.45, 114.50,
3
1
14.72, 126.96, 130.13, 146.72, 161.85, 172.08.
(
2E )-3-(Naphth-1-yl)prop-2-enoic Acid(2h): Colorless crystals. Yield:
ꢀ
24c
ꢀ
6
1
(
9%; m.p.: 212–213 C (lit.
ꢂ1
211–212 C); IR (KBr): 3250–2340, 1682,
1
616 cm ; H NMR (DMSO-d ): d 6.58 (d, 1H, J ¼ 15.8 Hz), 7.45–7.71
6
m, 3H), 7.85–8.07 (m, 3H), 8.18 (d, 1H, J ¼ 8.0 Hz), 8.38 (d, 1H,