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The Journal of Organic Chemistry
general procedure III and purified by column chromatography on silica gel and eluted with petroleum ether: ethyl
acetate: dichloromethane = 2:2:1 (v:v:v) to afford a white solid in 93% yield (62.1 mg). 1H NMR (400 MHz, CDCl3) δ
7.78-7.73 (m, 4H), 7.54-7.51 (m, 2H), 7.47-7.41 (m, 5H), 7.30 (d, J = 1.9 Hz, 1H), 7.19-7.12 (m, 2H), 6.54 (d, J = 2.8
Hz, 1H), 3.88 (d, J = 14.0 Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 154.6 (d, JC-P = 1.0 Hz), 148.6 (d, JC-P = 7.8
Hz), 132.1 (d, JC-P = 2.8 Hz), 131.8 (d, JC-P = 100.5 Hz), 131.1 (d, JC-P = 9.5 Hz), 128.582 (d, JC-P = 2.2 Hz), 128.581
(d, JC-P = 11.9 Hz), 123.7, 122.6, 120.6, 110.8, 106.0 (d, JC-P = 6.1 Hz), 31.8 (d, JC-P = 67.7 Hz); 31P NMR (162 MHz,
CDCl3) δ 27.8.
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(benzo[b]thiophen-2-ylmethyl)diphenylphosphine oxid (4p). The title compound was prepared according to the
general procedure III and purified by column chromatography on silica gel and eluted with petroleum ether: ethyl
acetate: dichloromethane = 2:2:1 (v:v:v) to afford a white solid in 70% yield (48.7 mg) , m.p. 254.2-255.9 oC. 1H NMR
(400 MHz, CDCl3) δ 7.79-7.74 (m, 4H), 7.68 (d, J = 7.6 Hz, 1H), 7.62 (d, J = 7.4 Hz, 1H), 7.56-7.52 (m, 2H),
7.49-7.45 (m, 4H), 7.29-7.21 (m, 3H), 3.94 (d, J = 13.2 Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 139.8, 139.7 (d,
JC-P = 2.5 Hz), 133.1 (d, JC-P = 8.5 Hz), 132.1 (d, JC-P = 2.5 Hz), 131.7 (d, JC-P = 99.0 Hz), 131.1 (d, JC-P = 9.1 Hz),
128.7 (d, JC-P = 11.7 Hz), 124.5 (d, JC-P = 7.6 Hz), 124.1, 123.9, 123.1, 121.9, 33.3 (d, JC-P = 67.4 Hz); 31P NMR (162
MHz, CDCl3) δ 28.4. HRMS (ESI, positive mode): C21H18OPS for [M+H]+, calculated 349.0810, found 349.0803.
diphenyl(quinolin-6-ylmethyl)phosphine oxide (4q). The title compound was prepared according to the general
procedure III and purified by column chromatography on silica gel and eluted with petroleum ether: ethyl acetate:
o
1
dichloromethane = 1:2:2 (v:v:v) to afford a white solid in 91% yield (62.2 mg), m.p. 229.7-230.3 C. H NMR (400
MHz, CDCl3) δ 8.85 (d, J = 3.2 Hz, 1H), 8.02 (d, J = 8.4 Hz, 1H), 7.90 (d, J = 8.8 Hz, 1H), 7.74-7.69 (m, 4H), 7.66 (s,
1H), 7.54-7.50 (m, 2H), 7.47-7.42 (m, 4H), 7.39-7.33 (m, 2H), 3.84 (d, J = 14.0 Hz, 2H); 13C{1H} NMR (100 MHz,
CDCl3) δ 150.2, 147.2 (d, JC-P = 2.1 Hz), 135.8, 132.0 (d, JC-P = 98.8 Hz), 131.9 (d, JC-P = 2.6 Hz), 131.7 (d, JC-P = 4.3
Hz), 131.1 (d, JC-P = 9.1 Hz), 129.7 (d, JC-P = 8.3 Hz), 129.3 (d, JC-P = 1.6 Hz), 128.8 (d, JC-P = 6.2 Hz), 128.5 (d, JC-P
=
31
11.7 Hz), 128.0 (d, JC-P = 2.7 Hz), 121.2, 38.1 (d, JC-P = 65.2 Hz); P NMR (162 MHz, CDCl3) δ 29.2. HRMS (ESI,
positive mode): C22H19NOP for [M+H]+, calculated 344.1199, found 344.1168.
benzyldi-p-tolylphosphine oxide (4r)27. The title compound was prepared according to the general procedure III
and purified by column chromatography on silica gel and eluted with petroleum ether: ethyl acetate: dichloromethane =
1
2:2:1 (v:v:v) to afford a white solid in 80% yield (51.2 mg). H NMR (400 MHz, CDCl3) δ 7.50-7.45 (m, 4H),
7.15-7.08 (m, 7H), 7.03-7.01 (m, 2H), 3.53 (d, J = 13.6 Hz, 2H), 2.28 (s, 6H); 13C{1H} NMR (100 MHz, CDCl3) δ
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