12924
M. L. N. Rao et al. / Tetrahedron 63 (2007) 12917–12926
(
2
7
400 MHz, CDCl ): d 3.78 (s, 3H), 6.87–6.89 (d,
3
4.2.44. 1,4-Phenylenebis(4-methylphenyl)methanone
ꢀ
1
H, J¼8.8 Hz), 7.03–7.06 (m, 1H), 7.53–7.59 (m, 2H),
(3.15a). Mp 173–176 C; H NMR (400 MHz, CDCl ):
3
1
3
.79–7.81 (d, 2H, J¼6.8 Hz);
C NMR (100 MHz,
d 2.38 (s, 6H), 7.22–7.24 (d, 4H, J¼8.0 Hz), 7.67–7.69 (d,
1
3
CDCl ): d 55.3, 113.5, 127.7, 130.4, 131.4, 133.3, 133.9,
3
1
(
4H, J¼8.0 Hz), 7.78 (s, 4H);
C NMR (100 MHz,
CDCl ): d 21.6, 129.1, 129.5, 130.3, 134.2, 140.7, 143.8,
3
ꢂ1
43.6, 162.9, 186.7; IR (cm ): 1628; MS (FAB): 219
M +1).
+
ꢂ1
+
195.8; IR (cm ): 1646; MS (FAB): 315 (M +1).
1
9d
15b
4
Mp 93–94 C (lit.
.2.37. (4-Fluorophenyl)(2-thienyl)methanone (3.8a).
95–96 C); H NMR (400 MHz,
4.2.45. 1,4-Phenylenebis(4-fluorophenyl)methanone
ꢀ
CDCl ): d 7.07–7.12 (m, 3H), 7.54–7.66 (m, 2H), 7.81–
.84 (m, 2H); C NMR (100 MHz, CDCl ): d 115.4,
3
15.6, 127.9, 131.6, 131.7, 134.2, 134.6, 143.2, 163.9,
66.4, 186.6; IR (cm ): 1628; MS (FAB): 207 (M +1).
19e
ꢀ
1
ꢀ
(3.16a). Mp 208–210 C; H NMR (400 MHz, CDCl ): d
3
7.10–7.26 (m, 4H), 7.72–7.86 (m, 8H); C NMR (100 MHz,
CDCl ): d 115.6, 115.8, 129.6, 132.7, 132.8, 140.5, 164.4,
166.9, 194.4; IR (cm ): 1647; MS (FAB): 323 (M +1).
1
1
3
3
1
3
7
1
1
3
ꢂ1
+
ꢂ1
+
1
7a
1
4 (4.1a). H NMR (400 MHz,
CDCl ): d 2.58 (s, 3H), 7.41–7.56 (m, 3H), 7.92–7.94 (m,
2H); C NMR (100 MHz, CDCl ): d 26.6, 128.3, 128.5,
133.1,137.1,198.1;IR(cm ):1684;MS(FAB):121(M +1).
.2.46. 1-Phenylethanone
6
g
4
Mp 93–95 C; H NMR (400 MHz, CDCl ): d 7.09–7.11
.2.38. (4-Chlorophenyl)(2-thienyl)methanone (3.9a).
ꢀ
3
13
1
3
3
ꢂ1
+
(
(
t, 1H, J¼4.9 Hz), 7.39–7.41 (d, 2H, J¼8.6 Hz), 7.54–7.56
d, 1H, J¼3.7 Hz), 7.66–7.67 (d, 1H, J¼4.9 Hz), 7.73–
1
3
20a
1
7
d 128.0, 128.7, 130.5, 134.5, 134.7, 136.3, 138.6, 143.1,
.75 (d, 2H, J¼8.3 Hz); C NMR (100 MHz, CDCl ):
4.2.47. 1-(4-Methylphenyl)ethanone (4.2a). H NMR
(400 MHz, CDCl ): d 2.38 (s, 3H), 2.55 (s, 3H), 7.22–7.24
3
3
ꢂ1
+
13
1
86.9; IR (cm ): 1628; MS (FAB): 223 (M +1).
(d, 2H, J¼7.8 Hz), 7.82–7.84 (d, 2H, J¼8.1 Hz); C NMR
(100 MHz, CDCl ): d 21.6, 26.5, 128.4, 129.2, 134.7,
143.8, 197.8; IR (cm ): 1680; MS (FAB): 135 (M +1).
3
1
5b
ꢂ1
+
4
.2.39. 1,3-Phenylenebis(phenyl)methanone
ꢀ
(3.10a).
Mp 96–98 C; H NMR (400 MHz, CDCl ): d 7.39–7.43
1
3
2
0b
1
(
t, 4H, J¼7.1 Hz), 7.50–7.56 (m, 3H), 7.73–7.75 (d, 4H,
4.2.48. 1-(4-Methoxyphenyl)ethanone (4.3a). H NMR
(400 MHz, CDCl ): d 2.52 (s, 3H), 3.83 (s, 3H), 6.88–6.91
1
3
J¼8.3 Hz), 7.93–7.95 (d, 2H, J¼7.6 Hz), 8.11 (s, 1H);
C
NMR (100 MHz, CDCl ): d 128.4, 128.4, 130.0, 131.1,
3
1
3
(d, 2H, J¼6.8 Hz), 7.88–7.91 (d, 2H, J¼6.8 Hz); C NMR
3
ꢂ1
1
(
32.8, 133.4, 136.8, 137.7, 195.8; IR (cm ): 1655; MS
FAB): 287 (M +1).
(100 MHz, CDCl ): d 26.3, 55.4, 113.6, 130.3, 130.5,
3
+
ꢂ1
+
163.5, 196.7; IR (cm ): 1675; MS (FAB): 151 (M +1).
9
d
1
4
.2.40. 1,3-Phenylenebis(4-methylphenyl)methanone
ꢀ
4.2.49. 1-Phenyl-1-propanone
(4.4a).
H
NMR
1
(
3.11a). Mp 118–120 C; H NMR (400 MHz, CDCl ):
3
(400 MHz, CDCl ): d 1.20 (t, 3H, J¼7.3 Hz), 2.98 (q, 2H,
3
d 2.37 (s, 6H), 7.21–7.24 (d, 4H, J¼8.0 Hz), 7.53–7.56 (t,
J¼7.1 Hz), 7.41–7.45 (t, 2H, 8.0 Hz), 7.50–7.54 (t, 1H,
1
3
1
H, J¼7.8 Hz), 7.66–7.68 (d, 4H, J¼8.3 Hz), 7.91–7.94
J¼7.3 Hz), 7.93–7.95 (d, 2H, J¼7.8 Hz);
C NMR
(100 MHz, CDCl ): d 8.1, 31.7, 127.9, 128.5, 132.8, 136.8,
3
1
3
(m, 2H), 8.07–8.08 (m, 1H);
CDCl ): d 21.6, 128.3, 129.1, 130.2, 130.9, 133.1, 134.2,
C NMR (100 MHz,
ꢂ1
+
200.8; IR (cm ): 1687; MS (FAB): 135 (M +1).
3
ꢂ1
1
(
38.0, 143.7, 195.6; IR (cm ): 1656; MS (FAB): 315
M +1).
+
19b
1
4.2.50. 1-(4-Methylphenyl)-1-propanone
(4.5a).
H
NMR (400 MHz, CDCl ): d 1.19 (t, 3H, J¼7.1 Hz), 2.38
3
4
.2.41. 1,3-Phenylenebis(4-methoxyphenyl)methanone
ꢀ
(s, 3H), 2.98 (q, 2H, J¼7.3 Hz), 7.21–7.24 (d, 2H,
1
13
(
3.12a). Mp 136–138 C; H NMR (400 MHz, CDCl ):
3
J¼8.3 Hz), 7.83–7.85 (d, 2H, J¼8.0 Hz);
C NMR
(100 MHz, CDCl ): d 8.2, 21.5, 31.6, 128.0, 129.1, 134.3,
3
d 3.85 (s, 6H), 6.93–6.95 (d, 4H, J¼7.1 Hz), 7.56–7.59 (t,
ꢂ1
+
1
H, J¼7.8 Hz), 7.80–7.82 (d, 4H, J¼7.3 Hz), 7.92–7.93
143.5, 200.5; IR (cm ): 1685; MS (FAB): 149 (M +1).
1
3
(d, 2H, J¼7.6 Hz), 8.05 (s, 1H); C NMR (100 MHz,
CDCl ): d 55.4, 113.6, 128.3, 129.5, 130.5, 132.5,
2
0c
1
4.2.51. 1-(4-Methoxyphenyl)-1-propanone
(4.6a). H
3
ꢂ1
1
(
32.6, 138.3, 163.4, 194.6; IR (cm ): 1651. HRMS
ES ) for (M+H) C H O , calcd: 347.1283; found:
NMR (400 MHz, CDCl ): d 1.18 (t, 3H, J¼7.3 Hz), 2.92
3
+
(q, 2H, J¼7.3 Hz), 3.83 (s, 3H), 6.88–6.90 (d, 2H,
2
2 19 4
1
3
3
47.1284.
J¼8.8 Hz), 7.90–7.92 (d, 2H, J¼8.8 Hz);
C NMR
100 MHz, CDCl ): d 8.4, 31.4, 55.4, 113.6, 130.0, 130.2,
(
163.3, 199.4; IR (cm ): 1679; MS (FAB): 165 (M +1).
3
1
5b
ꢂ1
+
4
.2.42. 1,3-Phenylenebis(4-fluorophenyl)methanone
1
(
3.13a). H NMR (400 MHz, CDCl ): d 7.08–7.30 (m,
3
1
7f
1
4
7
H), 7.55–7.59 (t, 1H, J¼7.6 Hz), 7.77–7.80 (m, 4H),
4.2.52. 1-Phenyl-1-butanone
(4.7a).
H
NMR
1
3
.91–7.93 (d, 2H, J¼7.6 Hz), 8.05 (s, 1H); C NMR
(400 MHz, CDCl ): d 0.98 (t, 3H, J¼7.6 Hz), 1.75 (q, 2H,
3
(
100 MHz, CDCl ): d 115.5, 115.8, 128.6, 130.7, 132.6,
3
J¼7.3 Hz), 2.92 (t, 2H, J¼7.4 Hz), 7.41–7.45 (t, 2H, J¼
13
ꢂ1
132.7, 133.3, 137.7, 164.3, 166.8, 194.2; IR (cm ): 1655;
MS (FAB): 323 (M +1).
7.6 Hz), 7.50–7.55 (t, 1H, J¼7.3 Hz), 7.92–7.95 (d, 2H,
+
J¼7.6 Hz); C NMR (100 MHz, CDCl ): d 13.8, 17.7,
3
ꢂ1
4
0.4, 127.9, 128.4, 132.8, 137.0, 200.4; IR (cm ): 1685;
MS (FAB): 149 (M +1).
1
5b
+
4
Mp 158–160 C; H NMR (400 MHz, CDCl ): d 7.47–
7
7
CDCl ): d 128.4, 129.7, 130.0, 132.9, 136.8, 140.5, 196.0;
3
IR (cm ): 1653; MS (FAB): 287 (M +1).
.2.43. 1,4-Phenylenebis(phenyl)methanone
ꢀ
(3.14a).
1
3
2
0d
1
.51 (t, 4H, J¼7.8 Hz), 7.58–7.62 (t, 2H, J¼7.3 Hz), 7.80–
4.2.53. 1-(4-Methylphenyl)-1-butanone
(4.8a).
H
1
3
.82 (d, 4H, J¼8.5 Hz), 7.86 (s, 4H); C NMR (100 MHz,
NMR (400 MHz, CDCl ): d 0.92 (t, 3H, J¼7.6 Hz), 1.65–
3
1.71 (m, 2H), 2.33 (s, 3H), 2.84 (t, 2H, J¼7.1 Hz), 7.16–
7.18 (d, 2H, J¼8.3 Hz), 7.77–7.79 (d, 2H, J¼8.3 Hz);
ꢂ1
+