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F. Cohen, L. E. Overman / Tetrahedron: Asymmetry 9 (1998) 3213–3222
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elution with 30% to 50% CH2Cl2–hexanes) to give 700 mg (55%) of 13 as a red solid: H NMR (500
MHz, C6D6) (2.5:1 mixture of isomers) major: δ 6.89 (s, 1H, N_CHFc), 6.81 (s, 1H, ArH), 6.70 (s, 1H,
ArH), 4.92 (d, J=2.1 Hz, 1H, FcH), 4.26 (s, 5H, FcH5), 4.01 (m, 4H, FcH), 2.48 (s, 3H, ArMe), 2.14 (s,
3H, ArMe), 2.08 (s, 3H, ArMe); minor: 6.87 (s, 1H, N_CHFc), 6.48 (s, 1H, ArH), 6.43 (s, 1H, ArH),
5.23 (d, J=2.1 Hz, 1H, FcH), 4.31 (s, 5H, FcH5), 4.17 (t, J=2.3 Hz, 1H, FcH), 4.05 (d, J=2.1 Hz, 1H,
FcH), 2.32 (s, 3H, ArMe), 2.03 (s, 3H, ArMe), 1.94 (s, 3H, ArMe); 13C NMR (125 MHz, CD2Cl2) both
isomers: δ 176.5, 176.2, 147.3, 145.9, 136.2, 136.16, 131.0, 129.8, 128.8, 128.7, 128.5, 109.0, 108.1,
88.9, 78.1, 78.0, 71.4, 71.0, 70.7, 67.03, 66.99, 21.0, 19.7, 19.6, 18.8; FTIR (film) 3092, 1451, 1564,
1320, 817 cm−1. Anal. calcd for C40H40I2N2Fe2Pd2: C, 42.63; H, 3.58; N, 2.49. Found: C, 42.66; H,
3.55; N, 2.50.
5.7. (S)-Bis-µ-iodo-bis[ferrocenylmethyliden-2,6-diisopropylaniline(C,N)]dipalladium(II) (14)
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44% yield of a dark red solid. H NMR (500 MHz, CD2Cl2) (1.4:1 mixture of isomers): δ 7.83 (s,
0.7H, N_CH), 7.80 (s, 0.3H, N_CH), 7.26–7.04 (m, 3H ArH), 5.02 (d, J=2.2 Hz, 0.3H, FcH), 4.85
(d, J=2.2 Hz, 0.7H, FcH), 4.55–4.38 (m, 7H, FcH), 3.57 (septet, J=6.9 Hz, 0.74H, CH), 3.40 (septet,
J=6.9 Hz, 0.3 CH), 3.30 (septet, J=6.9 Hz, 0.7H, CH), 3.15 (septet, J=6.9 Hz, 0.3H, CH), 1.58 (d, J=6.9
Hz, 2H, Me), 1.40–1.25 (m, 7H, Me), 1.37 (d, J=6.9 Hz, 3H, Me), 1.33 (d, J=6.9 Hz, 3H, Me), 1.0
(d, J=6.9 Hz, 3H, Me), 1.05–0.96 (m, 3H, Me); 13C NMR (125 MHz, CD2Cl2) both isomers: δ 175.8,
175.7, 147.0, 141.8, 141.4, 127.4, 127.2, 123.5, 123.4, 123.3, 123.1, 78.2, 78.0, 71.0, 70.9, 70.8, 67.1,
67.0, 28.4, 28.1, 25.3, 24.9, 23.4, 22.5; FTIR (film) 3084, 1562, 1327, 1107, 815 cm−1. Anal. calcd for
C46H52N2I2Fe2Pd2: C, 45.62; H, 4.33; N, 2.31. Found: C, 45.73; H, 4.43; N, 2.29.
5.8. (S)-Bis-µ-iodo-bis[ferrocenylmethylidenaniline(C,N)]dipalladium(II) (15)
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50% yield of a red solid: H NMR (400 MHz, CD2Cl2) (1.4:1 mixture of isomers) δ 8.11 (s, 1H,
N_CHFc), 7.47–7.16 (m, 5H, ArH), 5.11 (d, J=1.9 Hz, 0.42H, FcH), 4.98 (d, J=1.9 Hz, 0.59H, FcH),
4.59–4.44 (m, 7H, FcH); 13C NMR (100 MHz, CD2Cl2) δ 174.4, 174.3, 151.3, 150.1, 129.0, 128.7,
127.1, 127.0, 123.8, 123.8, 108.5, 88.8, 79.0, 78.7, 71.5, 71.4, 67.5, 67.4; FTIR (KBr) 3083, 1556, 1458,
1319, 1206 cm−1. Anal. calcd for C34H28I2N2Fe2Pd2: C, 39.16; H, 2.71; N, 2.69. Found: C, 39.28; H,
2.65; N, 2.74.
5.9. (S)-Bis-µ-iodo-bis[ferrocenylmethyliden-4-trifluoromethylaniline(C,N)]dipalladium(II) (16)
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22% yield of a red solid: H NMR (400 MHz, CD2Cl2) (1.3:1 mixture of isomers) δ 8.20 (s, 1H,
N_CHFc), 7.72 (d, 1.2H, J=8.2 Hz, ArH), 7.63 (d, 0.30H, J=8.1 Hz, ArH), 7.43 (d, 1.4H, J=8.2 Hz,
ArH), 7.31 (d, 0.60H, J=8.2 Hz, ArH), 5.19 (s, 0.43H, FcH), 5.07 (s, 0.57H, FcH), 4.64–4.48 (m, 7H,
FcH); 13C NMR (100 MHz, CD2Cl2) δ 175.4, 126.3, 124.2, 88.5, 79.5, 79.3, 72.2, 71.6, 67.9; FTIR
(KBr) 1610, 1559, 1321 cm−1. Anal. calcd for C36H26F6I2N2Fe2Pd2: C, 36.68; H, 2.22; N, 2.38. Found:
C, 36.58; H, 2.22; N, 2.40.
5.10. (S)-Bis-µ-iodo-bis[ferrocenylmethyliden-4-methylaniline(C,N)]dipalladium(II) (17)
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57% of a red solid: H NMR (400 MHz, CD2Cl2) (mixture of isomers) δ 8.07 (s, 1H, N_CHFc),
7.25–7.05 (m, 4H, ArH), 5.09 (s, 0.5H, FcH), 4.98 (s, 0.5H, FcH), 4.58–4.45 (m, 7H, FcH); 13C NMR
(100 MHz, CD2Cl2) δ 173.6, 173.4, 148.4, 136.6, 136.5, 129.0, 128.8, 123.1, 122.9, 107.8, 107.4, 88.3,