JOURNAL OF SULFUR CHEMISTRY
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4.2.2. (Selenophen-2-yl)(thiophen-2-yl)methanol (2b)
Pale yellow solid; yield: 228 mg (94%); m.p. 58.0–60.0°C (petroleum ether/CH2Cl2) ([12]:
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m.p. 62.5°C). H NMR (600 MHz, CDCl3): δ 2.74 (d, JH,H = 3.6 Hz, OH), 6.30 (d,
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JH,H = 3.6 Hz, CH O), 6.97–7.01 (m, 1CHarom), 7.04–7.07 (m, 1CHarom), 7.17–7.19 (m,
1CHarom), 7.20–7.23 (m, 1CHarom), 7.30 (dd, 4JH,H = 1.2 Hz, 3JH,H = 5.4 Hz, 1CHarom),
7.99 (dd, JH,H = 1.2 Hz, JH,H = 5.4 Hz, 1CHarom) ppm. 13C{ H} NMR (150 MHz,
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CDCl3): δ 70.3 (CH O), 124.9, 125.5, 126.6, 126.9, 129.1, 130.9 (6CHarom), 147.5, 154.6
(2Carom) ppm. IR (KBr): υ 3500s (OH), 3414s, 3098m, 3069m, 2955w, 2920w, 2854w,
1815w, 1736w, 1673w, 1606w, 1543m, 1447m, 1372m, 1347m, 1292m, 1261s, 1217s, 1173m,
1125s, 1066m, 1014m, 986s, 856m, 834s, 807m, 755m, 698vs cm−1
4.2.3. (Furan-2-yl)(selenophen-2-yl)methanol (2c)
.
Isolated as a viscous oil turning brownish when stored at ambient conditions; yield:
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148 mg (65%). H NMR (600 MHz, CDCl3): δ 2.72 (d, JH,H = 4.8 Hz, OH), 6.07 (d,
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JH,H = 4.8 Hz, CH O), 6.31–6.33 (m, 1CHarom), 6.35–6.38 (m, 1CHarom), 7.17–7.19 (m,
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1CHarom), 7.20–7.24 (m, 1CHarom), 7.41–7.42 (m, 1CHarom), 8.00 (dd, JH,H = 0.6 Hz,
JH,H = 6.0 Hz, 1CHarom) ppm. 13C{ H} NMR (150 MHz, CDCl3): δ 68.1 (CH O), 107.2,
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110.3, 127.1, 129.1, 131.0, 142.5 (6CHarom), 151.7, 155.1 (2Carom) ppm. IR (KBr): υ 3430s
(OH), 3107w, 3050w, 2930w, 1720s, 1701s, 1502m , 1448m, 1369m, 1233m, 1144m, 1071m,
1011m, 986m, 922m, 805m, 739s, 691vs cm−1. All attempts to prepare this product as an
analytically pure sample were unsuccessful.
4.2.4. Phenyl(thiophen-2-yl)methanol (2d)
Pale yellow solid; yield: 177 mg (93%); m.p. 58.0–60.0°C (petroleum ether/CH2Cl2) ([12]:
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m.p. 62.5°C). H NMR (600 MHz, CDCl3): δ 2.53–2.56 (m, OH), 6.03–6.07 (m, CH O),
6.88–6.91 (m, 1CHarom), 6.94–6.98 (m, 1CHarom), 7.24–7.29 (m, 1CHarom), 7.31–7.35
(m, 1CHarom), 7.36–7.41 (m, 2CHarom), 7.43–7.49 (m, 2CHarom) ppm. 13C{ H} NMR
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(150 MHz, CDCl3): δ 72.4 (CH O), 124.8, 125.3, 126.3, 126.6, 127.9, 128.5 (8CHarom),
143.1, 148.1 (2Carom) ppm. IR (KBr): υ 3256s (OH), 2664w, 2357m, 2338m, 2145w, 1958w,
1894w, 1796w, 1768w, 1600w, 1486m, 1458m, 1435m, 1353m, 1280m, 1258m, 1201m,
1144m, 1033m, 1008vs, 916m, 853m, 824m, 786m, 726m, 694vs, 590m, 527m cm−1. Anal.
calcd for C11H10OS (190.26): C 69.44, H 5.30, S 16.85; found: C 69.45, H 5.31, S 16.95.
4.2.5. Phenyl(selenophen-2-yl)methanol (2e)
Pale yellow solid; yield: 161 mg (68%); m.p. 64.0–66.0°C ([13]: m.p. 60–61°C). 1H NMR
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(600 MHz, CDCl3): δ 2.58 (brs, OH), 6.04 (brs, CH O), 7.04–7.08 (m, 1CHarom), 7.19
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(dd, JH,H = 3.6 Hz, JH,H = 6.0 Hz, 1CHarom), 7.31–7.35 (m, 1CHarom), 7.37–7.41 (m,
2CHarom), 7.46–7.49 (m, 2CHarom), 7.97 (dd, 4JH,H = 1.2 Hz, 3JH,H = 6.0 Hz, 1CHarom
)
ppm. 13C{ H} NMR (150 MHz, CDCl3): δ 74.2 (CH O), 126.2, 126.6, 128.0, 128.5, 129.1,
130.6 (8CHarom), 143.5, 155.8 (2Carom) ppm. IR (KBr): υ 3215s (OH), 2866m, 2664w,
1958w, 1888w, 1784w, 1600w, 1587w, 1546w, 1496m, 1448s, 1328m, 1293m, 1258m,
1204m, 1195m, 1147m, 1081m, 1033m, 1021s, 922w, 821s, 758m, 707vs, 691vs, 637m,
580m cm−1. Anal. calcd for C11H10OSe (237.16): C 55.71, H 4.25; found: C 55.87, H 4.25.
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