3
510
M. H. Ali et al.
PAPER
1
4-Hydroxymethylphenyl Methyl Sulfoxide (2m)27
H NMR (300 MHz, CDCl ): d = 0.92 (t, J = 7.2 Hz, 3 H), 1.28–
3
1
1
.70 (m, 2 H), 1.68–1.78 (m, 2 H), 2.60 (t, J = 7.62 Hz, 2 H).
IR (film): 809, 958, 1010, 1026, 1202, 1365, 1406, 2915, 3022,
–
1
3
3062, 3352 cm .
C NMR (75 MHz, CDCl ): d = 13.7, 22.0, 24.6, 52.1.
3
1
H NMR (300 MHz, CDCl ): d = 2.67 (s, 3 H), 4.03 (br s, 1 H, OH),
3
Tetramethylene Sulfoxide (2c)
IR (film): 768, 995, 1096, 1212, 1284, 1408, 2877, 2974 cm .
4.70 (s, 2 H), 7.45–7.55 (m, 4 H).
–
1
13
C NMR (75 MHz, CDCl ): d = 43.6, 63.9, 123.8, 127.5, 143.3,
3
1
H NMR (300 MHz, CDCl ): d = 2.03-2.08 (m, 2 H), 2.43–2.47 (m,
145.3.
3
2
1
H), 2.87–2.92 (m, 4 H, CH CH ).
2 2
Benzyl Methyl Sulfoxide (2n)26
3
C NMR (75 MHz, CDCl ): d = 24.8, 53.5.
3
IR (film): 767, 1028, 1201, 1301, 1422, 1455, 1496, 2916, 2976,
–
1
3
031, 3056 cm .
2
-(Methylsulfinyl)butane (2e)
1
Diastereomeric mixture (~1:1).
H NMR (300 MHz, CDCl ): d = 2.45 (s, 3 H), 4.00 (2 d, J = 6 Hz,
3
2
H), 7.20–7.40 (m, 5 H).
IR (film): 943, 1023, 1152, 1214, 1383, 1404, 1460, 2879, 2935,
2
–
1
13
973 cm .
C NMR (75 MHz, CDCl ): d = 37.4, 60.3, 128.9, 129.4, 130.0,
3
1
130.5.
H NMR (300 MHz, CDCl ): d = 1.04 (2 t, J = 7.3 Hz, 3 H), 1.07 (t,
3
J = 7.4 Hz, 3 H), 1.21 (d, J = 6.84, 3 H), 1.27 (d, J = 6.84 Hz, 3 H),
1
2
Methyl 4-Nitrophenyl Sulfoxide (2o)28
.45 (m, 2 H), 1.84–1.87 (m, 2 H), 2.42 (m, 1 H), 2.53 (2 s, 6 H),
.69–2.71 (m, 1 H).
–
1
IR (film): 740, 849, 958, 1045, 1344, 1518, 2838, 2936, 3036 cm .
1H NMR (300 MHz, CDCl
): d = 2.80 (s, 3 H), 7.86 (d, J = 8.8 Hz,
H), 8.41 (d, J = 8.8 Hz, 2 H).
1
3
3
C NMR (75 MHz, CDCl ): d = 10.7, 10.9, 11.3, 11.4, 22.6, 23.2,
3
2
3
3.9, 34.4, 57.7, 58.3.
1
3
C NMR (75 MHz, CDCl ): d = 43.8, 124.5, 124.64, 149.5, 153.3.
3
Ethyl Phenyl Sulfoxide (2f)
IR (film): 748, 998, 1044, 1086, 1146, 1306, 1446, 1478, 2875,
2
1
Benzyl Phenyl Sulfoxide (2p)29
–1
935, 2979, 3057 cm .
IR (film): 690, 742, 925, 1026, 1283, 1441, 1516, 2924, 2976, 3060
–
1
cm .
H NMR (300 MHz, CDCl ): d = 1.20 (t, J = 6.8 Hz, 3 H), 2.72–
3
1
2
1
.98 (m, 2 H), 7.50–7.63 (m, 5 H).
H NMR (300 MHz, CDCl ): d = 3.97 (d, J = 12.5 Hz, 1 H), 4.10 (d,
3
3
J = 12.5 Hz, 1 H), 6.90–6.98 (m, 2 H), 7.21–7.28 (m, 3 H), 7.38–
C NMR (75 MHz, CDCl ): d = 6.3, 50.6, 124.6, 129.5, 131.3,
3
7
.48 (m, 5 H).
1
43.1.
1
3
C NMR (75 MHz, CDCl ) d = 63.4, 124.4, 128.2, 128.4, 128.8,
3
Allyl Methyl Sulfoxide (2h)24
IR (film): 741, 953, 1044, 1438, 1646, 2922, 3006, 3076 cm .
129.0, 130.3, 131.2, 142.5.
–
1
Thiooxachroman-4-one S-Oxide (2q)30
1
H NMR (300 MHz, CDCl ): d = 2.05 (s, 3 H), 3.48 (m, 2 H), 5.10–
3
IR (film): 773, 1036, 1183, 1283, 1326, 1441, 1586, 1690, 2894,
6
.20 (m, 3 H).
–
1
2
922, 2986, 3008, 3063 cm .
1
1
,4-Thioxane 4-Oxide (2i)25
H NMR (300 MHz, CDCl ): d = 2.86–2.95 (m, 1 H), 3.45–3.54 (m,
3
IR (film): 729, 826, 1014, 1039, 1095, 1274, 1320, 1382, 1403,
1
3 H), 7.70 (t, J = 7.5 Hz, 1 H), 7.80 (t, J = 7.5 Hz, 1 H), 7.90 (d,
J = 7.6 Hz, 1 H), 8.15 (d, J = 7.6 Hz, 1 H).
–
1
461, 2863, 2922, 2976 cm .
1
13
H NMR (300 MHz, CDCl ): d = 2.72–2.78 (m, 2 H), 2.91–3.0 (m,
C NMR (75 MHz, CDCl ): d = 30.7, 47.1, 128.9, 129.4, 129.6,
3
3
2
H), 3.80–3.87 (m, 2 H), 4.32–4.40 (m, 2 H).
132.6, 135.1, 145.9, 192.5.
1
3
C NMR (75 MHz, CDCl ): d = 46.2, 59.1.
3
Diphenyl Sulfoxide (2r)
IR (film): 708, 766, 1049, 1104, 1453, 1485, 3067 cm .
–
1
Methyl 4-Methylphenyl Sulfoxide (2k)26
1
IR (film): 812, 956, 1039, 1087, 1294, 1407, 1495, 1597, 2736,
H NMR (300 MHz, CDCl ): d = 7.30–7.60 (m, 10 H).
3
–1
2
921, 2993, 3045 cm .
13
C NMR (75 MHz, CDCl ): d = 126.8, 129.1, 131.0, 145.7.
3
1
H NMR (300 MHz, CDCl ): d = 2.41 (s, 3 H), 2.72 (s, 3 H), 7.32
3
(
d, J = 8.5 Hz, 2 H), 7.54 (d, J = 8.5 Hz, 2 H).
4-Bromophenyl Methyl Sulfoxide (2s)31
1
3
IR (film): 722, 816, 960, 1007, 1045, 1085, 1386, 1420, 1472, 2910,
C NMR (75 MHz, CDCl ): d = 21.3, 43.8, 123.5, 129.98, 141.5,
3
–1
2
995, 3044 cm .
1
42.3.
1
H NMR (300 MHz, CDCl ): d = 2.74 (s, 3 H), 7.53 (d, J = 8.7 Hz,
3
4
-Methoxyphenyl Methyl Sulfoxide (2l)26
2 H), 7.68 (d, J = 8.7 Hz, 2 H).
IR (film): 831, 957, 1027, 1090, 1179, 1255, 1303, 1497, 1578,
13
C NMR (75 MHz, CDCl ): d = 43.8, 125.2, 125.4, 132.5, 144.6.
–
1
3
1
595, 2839, 2974, 2990, 3004, 3104 cm .
1
H NMR (300 MHz, CDCl ): d = 2.70 (s, 3 H), 3.84 (s, 3 H), 7.04
3
Acknowledgment
(
d, J = 8.8 Hz, 2 H), 7.58 (d, J = 8.8 Hz, 2 H).
1
3
C NMR (75 MHz, CDCl ): d = 44.2, 55.8, 115.5, 126.1, 136.8,
M.H.A. thanks Prof. Bjorn Olesen for his suggestions during the
preparation of the manuscript.
3
1
62.2.
Synthesis 2007, No. 22, 3507–3511 © Thieme Stuttgart · New York