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POTKIN et al.
Ferrocenylmethyl 5-(4-methylphenyl)isoxazole-
NMR spectrum, δС, ppm: 20.26 (Me), 20.43 (Me),
67.17, 69.39, 69.46, 69.48, 69.66, 69.71, 71.45 (8CHСр +
2CH), 87.77, 87.85, 125.62, 150.54, 154.70 (8Сtert),
158.71 (C=O), 158.74 (C=O). Found, %: С 41.90; Н
2.61; Cl 22.05; N 4.54; S 9.65; Fe 8.54. C22H16Cl4FeN2O4S2.
Calculated, %: C 41.67; H 2.54; Cl 22.36; N 4.42; S
10.11; Fe 8.81. М 634.14.
3-carboxylate (17). Yield 75%, mp 104–105°C
(hexane). IR spectrum, v, cm–1: 3138, 3092, 3033,
2975, 2921, 2858, 1729; 1717 (С=О); 1614, 1597,
1570, 1513, 1468, 1447, 1413, 1293, 1267, 1249,
1190, 1141, 1104, 1037, 1001, 972, 874, 852, 825,
1
802, 782, 499, 482. Н NMR spectrum, δ, ppm: 2.40 s
(3H, Ме), 4.21 s (5HСр), 4.22 t (2HСр, J 1.8 Hz), 4.38 t
(2HСр, J 1.8 Hz), 5.22 s (2H, CH2), 6.84 s (1Нisoxazole),
7.27 d (2НAr, J 8.1 Hz), 7.67 d (2НAr, J 8.1 Hz). 13С
NMR spectrum, δС, ppm: 21.66 (Ме), 64.58 (CH2),
68.79 (5CHСр), 69.20 (2CHСр), 70.19 (2CHСр), 99.51
(СНisoxazole), 125.98 (2СНAr), 129.93 (2СНAr), 80.38,
124.08, 141.32, 156.97, 172.00 (5Сtert), 160.07 (C=O).
Found, %: C 65.98; H 4.59; N 3.4; Fe 14.02.
C22H19FeNO3. Calculated, %: C 65.86; H 4.77; N 3.49;
Fe 13.92. М 401.24.
1,1'-Bis[1-(5-phenylisoxazole-3-carboxyl)ethyl]-
ferrocene (21). Yield 65%, mp 88–89°C (benzene–
hexane, 2 : 1). IR spectrum, ν, cm–1: 3146, 3130, 3067,
3042, 3003, 2979, 2929, 2871; 1722 (С=О); 1613,
1593, 1572, 1446, 1370, 1314, 1295, 1252, 1240,
1189, 1145, 1098, 1068, 1026, 993, 948, 935, 858,
1
835, 767, 690, 676, 480. Н NMR spectrum, δ, ppm:
3
1.73 d (6H, 2Me, J 6.5 Hz). 4.23 s (4H Ср), 4.33 s
(2СHСр), 4.41 s (2СHСр), 6.10–6.19 m (2H, 2CH),
7.42–7.51 m (6НAr), 7.75–7.82 m (4НAr). 13С NMR
spectrum, δС, ppm: 20.38 (Me), 20.45 (Me), 67.26,
3,4,4-Trichloro-1-cymantrenylbut-3-en-1-yl 4,5-
dichloroisothiazole-3-carboxylate (18). Yield 83%,
viscous oil. IR spectrum, ν, cm–1: 3114, 2928; 2021,
1935 (СОligands); 1739 (С=О); 1403, 1353, 1212, 1084,
69.38, 69.40, 69.68, 69.74, 71.18, 71.20 (8CHСр
+
2CH), 100.12 (2СНisoxazole), 126.05 (4СНAr), 129.25
(4СНAr), 130.90 (2СНAr), 87.94, 88.00, 126.77,
157.21, 171.81 (8Сtert), 159.60 (2C=O). Found, %: C
65.47; H 4.05; N 4.59; Fe 9.64. C34H28FeN2O6. Cal-
culated, %: C 65.32; H 4.11; N 4.76; Fe 9.49. М 616.45.
1
1034, 970. Н NMR spectrum, δ, ppm: 2.82–3.20 m
(2H, СН2), 4.85 s (2HСр), 4.90 s (2HСр), 6.17–6.27 m
(1H, СН). 13С NMR spectrum, δС, ppm: 46.66 (СН2),
66.25 (СН), 83.40 (2СНСр), 83.47 (2СНСр), 101.99,
110.00, 126.20, 131.08, 156.29, (5Сtert), 160.65 (C=O),
225.79 and 226.50 (3СОligands). Found, %: С 34.94; Н
1.49; Cl 31.27; N 2.12; S 5.28; Mn 9.42.
C16H7Cl5MnNO5S. Calculated, %: C 34.47; Н 1.27; Cl
31.79; N 2.51; S 5.75; Mn 9.85. М 557.48.
1,1'-Bis{1-[5-(4-methylphenyl)isoxazole-3-car-
boxyl]ethyl}ferrocene (22). Yield 71%, mp 91–93°C
(benzene–hexane, 2 : 1). IR spectrum, ν, cm–1: 3133,
3088, 3033, 2992, 2945, 2923, 2855; 1721 (С=О);
1615, 1594, 1567, 1509, 1444, 1411, 1380, 1315,
1293, 1240, 1189, 1143, 1114, 1060, 1042, 993, 948,
836, 813, 780, 498. 1Н NMR spectrum, δ, ppm: 1.72 d
(6H, 2Me, 3J 6.5 Hz), 2.40 s (6H, 2Ме), 4.22 s (4HCp),
4.32 s (2СHCp), 4.40 s (2СHCp), 6.10–6.17 m (2H,
2CH), 6.85 s (1Нisoxazole), 6.86 s (1Нisoxazole), 7.27 d
1,1'-Bis[(4,5-dichloroisothiazole-3-carboxyl)me-
thyl]ferrocene (19). Yield 70%, mp 136–138°C
(benzene–hexane, 2 : 1). IR spectrum, ν, cm–1: 3106,
2959, 2922, 2852; 1727 (С=О); 1443, 1405, 1356,
1269, 1241, 1221, 1078, 1043, 958. 1Н NMR
spectrum, δ, ppm: 4.23 s (4HСр), 4.39 s (4HСр), 5.21 s
(4H, CH2). 13С NMR spectrum, δС, ppm: 64.39
(2CH2), 69.81 (4CHСр), 70.60 (4CHСр), 81.19, 125.8,
150.66, 154.30 (8Ctert), 158.99 (2С=O). Found, %: С
40.14; Н 2.21; Cl 23.05; N 4.15; S 10.19; Fe 9.04.
C20H12Cl4FeN2O4S2. Calculated, %: C 39.63; H 2.00;
Cl 23.40; N 4.62; S 10.58; Fe 9.21. М 606.09.
3
3
(4НAr, J 8.1 Hz), 7.68 d (4НAr, J 8.1 Hz). 13С NMR
spectrum, δС, ppm: 20.42 (Me), 20.49 (Me), 21.67
(2Ме), 67.28, 69.38, 69.41, 69.69, 69.75, 71.10, 71.13
(8CHCp + 2CH), 99.54 (2СНisoxazole), 126.02 (4СНAr),
129.95 (4СНAr), 88.01, 88.07, 124.14, 141.33, 157.18,
172.04 (10Сtert), 159.71 (2C=O). Found, %: C 66.33; H
4.44; N 4.41; Fe 9.20. C36H32FeN2O6. Calculated, %: C
66.25; H 4.58; N 4.54; Fe 9.06. М 644.51.
1,1'-Bis[1-(4,5-dichloroisothiazole-3-carboxyl)-
ethyl]ferrocene (20). Yield 71%, mp 54–56°C (benzene–
hexane, 2 : 1). IR spectrum, ν, cm–1: 3090, 2983, 2941,
2875, 2855; 1717 (С=О); 1403, 1352, 1315, 1217,
1,1'-Bis[2-(4,5-dichloroisothiazole-3-carboxyl)-2-
butyl]ferrocene (23). 0.03 g (1.2 mmol) of NaH
powder was added at –10°C and vigorous stirring to a
solution of 0.15 g of (0.45 mmol) of ferrocene tertiary
diol 13 in 50 mL of anhydrous tetrahydrofuran. After
incubation at that temperature during 2 h, 0.22 g
(1 mmol) of 4,5-dichloroisothiazole-3-carboxylic acid
1
1079, 1059, 970. Н NMR spectrum, δ, ppm: 1.62–
1.79 m (6H, 2Me), 4.19 s (4СH Ср), 4.30 br.s (2СHСр),
4.34–4.40 m (2СHСр), 6.01–6.20 m (2H, 2CH). 13С
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 2 2016