8
5-N,N-Dimethylamino-2,2´-bithiophene (5d) : yellow solid, mp 34-36 C. Yield. 69%.
o
32
5-N,N-Diethylamino-2,2´-bithiophene (5e) : yellow liquid. Yield 64%.
5-N,N-Diisopropylamino-2,2´-bithiophene (5f): yellow liquid. Yield 53%. Anal. Calcd for C H NS : C,
14 19
2
1
63.38; H, 7.16; N, 5.28; S, 24.17. Found: C, 63.41; H, 7.27; N, 5.30; S, 24.16. H ΝΜR δ (CDCl ) 1.22
H
3
(12H, d, J = 6.7 Hz, 4xCH ), 3.61 (2H, sep, J = 6.7 Hz, 2xCH), 6.15 (1H, d, J = 3.7 Hz, 4-H), 6.89 (1H, d,
3
J = 3.7 Hz, 3-H), 6.96 (1H, m, 4´-H), 7.00 (1H, dd, J = 3.7 and 1.2 Hz, 3´-H), 7.09 (1H, dd, J = 4.8 and 1.2
13
Hz, 5´-H). C ΝΜR δ (CDCl ) 20.87, 50.88, 113.44, 121.40, 121.96, 122.39, 125.53, 127.50, 138.82,
C
3
+
153.10. ΜS (EI, 70 eV): m/z (%) 265 (M , 54), 250 (16), 222 (27), 208 (26), 180 (54), 69 (100). IR
-1
(liquid film)/cm 3070, 2970, 2930, 2870, 1557, 1511, 1489, 1380, 1366, 1331, 1316, 1271, 1247,
ν
max
3
-1
-
1230, 1190, 1157, 1125, 1055, 1014, 920, 885, 839, 798, 757, 688. UV λ
/nm (log ε /dm mol cm
max
max
1
) 341.0 (11494), 246.5 (4481), 213.5 (3633).
o
5-Piperidino-2,2´-bithiophene (5g): pale yellow solid, mp 59-60 C (light petroleum). Yield 79%. Anal.
Calcd for C H NS : C, 62.64; H, 6.02; N, 5.62; S, 25.73. Found: C, 62.59; H, 6.09; N, 5.56; S,
2
13 15
1
26.03. Η ΝΜR δ (CDCl ) 1.50-1.64 (2H, m, CH ), 1.68-1.80 (4H, m, 2xCH ), 3.10-3.20 (4H, m,
H
3
2
2
2xCH ), 6.00 (1H, d, J = 4.0 Hz, 4-H), 6.89 (1H, d, J = 4.0 Hz, 3-H), 6.95-7.00 (2H, m, 3´ and 4´-H),
2
13
7.05-7.11 (1H, m, 5´-H). C ΝΜR δ (CDCl ) 23.60, 25.09, 52.58, 105.48, 121.39, 122.43, 123,04,
C
3
+
127.51, 138.48, 158.44. ΜS (EI, 70 eV): m/z (%) 249 (M , 100), 69 (9), 57 (14). IR ν
(liquid
max
-1
film)/cm 2939, 2826, 1556, 1514, 1488, 1446, 1301, 1276, 1242, 1192, 1121, 1068, 1013, 894, 826, 810,
3 -1 -1
/nm (log ε /dm mol cm ) 343.0 (18039), 241.5 (4914), 214.0 (6102).
769, 682. UV λ
max
max
o
5-N,N-Dicyclohexylamino-2,2´-bithiophene (5h): pale yellow solid, mp 52-55 C (light petroleum). Yield
1
63%. Η ΝΜR δ (CDCl ) 0.90-1.82 (20H, m, 10xCH ), 3.00-3.20 (2H, m, CH), 6.19 (1H, d, J = 3.7 Hz,
H
3
2
4-H), 6.86 (1H, d, J = 3.7 Hz, 3-H), 6.90-7.25 (2H, m, 3´ and 4´-H), 7.04 (1H, br d, J = 5.2 Hz, 5´-H). ΜS
+
(EI, 70 eV): m/z (%) 345 (M , 100), 302 (4), 263 (31), 236 (5), 220 (9), 205 (8), 192 (5), 180 (57), 153,
-1
(liquid film)/cm 2940, 2860, 1520, 1480, 1450, 1380,
(5), 121 (8), 96 (14), 81 (11), 55 (30). IR ν
max
1340, 1260, 1240, 1200, 1130, 1120, 1110, 1050, 1020, 980, 900, 840, 800, 760, 715, 690.
o
5-(4-Methoxyanilino)-2,2´-bithiophene (5i): pale green solid, mp 113-115 C (ether). Yield 14%. Anal.
Calcd for C H NOS : C, 62.71; H, 4.52; N, 4.87; S, 22.32. Found: C, 62.84; H, 4.61; N, 4.81; S,
15 13
2
1
22.72. Η ΝΜR δ (CDCl ) 3.80 (3H, s, OCH ), 6.50 (1H, d, J = 3.7 Hz, 4-H), 6.85 (2H, d, J = 8.9 Hz,
H
3
3
2´´and 6´´-H or 3´´and 5´´-H), 6.94 (1H, d, J = 3.7 Hz, 3-H), 6.97 (2H, d, J = 8.9 Hz, 3´´and 5´´-H or
2´´and
6´´- H), 7.00 (1H, m, 4´-H), 7.05 (1H, dd, J = 3.6 and 1.2 Hz, 3´-H), 7.16 (1H, dd, J = 5.0 and
13
1.2 Hz, 5´-H). C ΝΜR δ (CDCl ) 55.62, 114.74, 115.49, 117.54, 122.35, 122.45, 123.34, 127.63,
C
3
+
127.92, 137.99, 138.36, 147.29, 154.27. ΜS (EI, 70 eV): m/z (%) 287 (M , 100), 272 (70), 210 (9), 185
-1
(liquid film)/cm 1514, 1462, 1441, 1349, 1298, 1249,
(11), 121, (13), 96 (14), 77 (6), 63 (7). IR ν
max
3
-1
-1
1165, 1102, 1040, 916, 835, 789. UV λ
/nm (log ε /dm mol cm ) 365.5 (19900), 245.0 (10596),
max
max