Helvetica Chimica Acta – Vol. 91 (2008)
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C36H52Cl2CoFeN2O2 (730): C 59.19, H 7.17, Cl 9.71, Co 8.07, Fe 7.64, N 3.83, O 4.38; found: C 59.15, H 7.15,
Cl 9.69, Co 8.00, Fe 7.62, N 3.79, O 4.36.
Trichloro(cobalt){m-{{2,2’-{(1R,2R)-cyclohexane-1,2-diylbis[(nitrilo-kN)methylidyne]}bis[4,6-bis(1,1-
dimethylethyl)phenolato-kO:kO]}(2ꢀ)}}iron (e). IR (KBr): 2954, 2866, 1634, 1609, 1511, 1459, 1365,
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1251, 1208, 1169, 1035, 985, 834, 785, 734, 640, 597. H-NMR (400 MHz, (D6)DMSO): 1.27( s, 18 H);
1.55 – 1.68 (m, 2 H); 1.7 1 (s, 18 H); 1.86 – 1.95 (m, 4 H); 1.9 – 2.20 (m, 2 H); 3.0 – 3.2 (m, 2 H); 3.5 – 3.8 (m,
2 H); 7.41 (d, J ¼ 2.4, 2 H); 7.59 (d, J ¼ 2.4 2 H); 7.76 (s, 2 H). 13C-NMR (400 MHz, (D6)DMSO): 24.5;
25.8; 29.3; 30.9; 31.5; 35.7; 69.21; 119.3; 128.4; 134.1; 142.3; 158.5; 162.1; 164.8. FAB-MS: 762.7
(C36H52Cl3CoFeN2Oþ2 ; calc. 764). Anal. calc. for C36H52Cl3CoFeN2O2 (764): C 56.90, H 7.10, Cl 13.62, Co
7.55, Fe 7.15, N 3.59, O 4.10; found: C 56.85, H 7.13, Cl 13.66, Co 7.60, Fe 7.20, N 3.62, O 4.09.
{m-{{2,2’-{(1R,2R)-cyclohexane-1,2-diylbis[(nitrilo-kN)methylidyne]}bis[4,6-bis(1,1-dimethylethyl)-
phenolato-kO:kO]}(2ꢀ)}}[di(nitrato-kN)zinc]cobalt (f). IR (KBr): 2950, 2863, 1635, 1608, 1523, 1461,
1361, 1253, 1200, 1172, 1026, 926, 833, 783, 744, 640, 597. 1H-NMR (400 MHz, (D6)DMSO): 1.25 (s, 18 H);
1.54 – 1.64 (m, 2 H); 1.7 1 (s, 18 H); 1.80 – 1.90 (m, 4 H); 1.95 – 1.97( m, 2 H); 3.1 – 3.2 (m, 2 H); 3.5 – 3.6
(m, 2 H); 7 .40 d(, J ¼ 2.4, 2 H); 7.42 (d, J ¼ 2.4, 2 H); 7.74 (s, 2 H). 13C-NMR (400 MHz, (D6)DMSO):
24.3; 25.1; 29.5; 30.5; 31.5; 33.5; 67.0; 69.2; 118.5; 128.6; 129.0; 135.8; 141.7; 161.8; 164.4. FAB-MS: 791.8
(C36H52CoN4O8Znþ; calc. 792). Anal. calc. for C36H52CoN4O8Zn (793): C 54.52, H 6.61, Co 7.43, N 7.06, O
16.14, Zn 8.24; found: C 54.50, H 6.65, Co 7.39, N 7.10, O 16.20, Zn 8.20.
{m-{{2,2’-{(1R,2R)-Cyclohexane-1,2-diylbis[(nitrilo-kN)methylidyne]}bis[4,6-bis(1,1-dimethylethyl)-
phenolato-kO:kO]}(2ꢀ)}}[di(nitrato-kN)nickel]cobalt (g). IR (KBr): 2950, 2866, 1616, 1527, 1434, 1384,
1253, 1203, 1172, 871, 833, 783, 574, 543. 1H-NMR (400 MHz, (D6)DMSO): 1.27( s, 18 H); 1.54 – 1.58 (m,
2 H); 1.7 3 (s, 18 H); 1.80 – 1.85 (m, 4 H); 1.96 – 1.97( m, 2 H); 3.0 – 3.1 (m, 2 H); 3.5 – 3.6 (m, 2 H); 7 .41 (d,
J ¼ 2.4, 2 H); 7.43 (d, J ¼ 2.4, 2 H); 7.77 s(, 2 H). Anal. calc. for C36H52CoN4NiO8 (786): C 54.98, H 6.66,
Co 7.49, N 7.12, Ni 7.46, O 16.28; found: C 54.95, H 6.54, Co 7.45, N 7.09, Ni 7.45, O 16.25.
{m-2,2’-{(1R,2R)-Cyclohexane-1,2-diylbis[(nitrilo-kN)methylidyne]}bis[4,6-bis(1,1-dimethylethyl)-
phenolato-kO:kO](2ꢀ)}}bis(nitrato-kN)dicobalt (h). IR (KBr): 2950, 2863, 1635, 1608, 1523, 1461, 1361,
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1253, 1200, 1172, 1026, 926, 833, 783, 744, 640, 597. H-NMR (400 MHz, (D6)DMSO): 1.24 (s, 18 H);
1.55 – 1.68 (m, 2 H); 1.69 (s, 18 H); 1.86 – 1.95 (m, 2 H); 1.96 – 2.20 (m, 2 H); 3.0 – 3.2 (m, 2 H); 3.5 – 3.8
(m, 2 H); 7 .40 d(, J ¼ 2.4, 2 H); 7.59 (d, J ¼ 2.4, 2 H); 7.74 (s, 2 H). 13C-NMR (400 MHz, (D6)DMSO):
24.3; 25.1; 29.5; 30.4; 31.5; 33.5; 35.7; 66.9; 69.2; 118.5; 128.6; 129.0; 135.8; 141.6; 161.8; 164.4. FAB-MS:
785.3 (C36H52Co2N4Oþ8 ; calc. 786.2). Anal. calc. for C36H52Co2N4O8 (786): C 54.96, H 6.66, Co 14.98, N
7.12, O 16.27; found: C 54.55, H 6.67, Co 15.00, N 7.15, O 16.30.
Butyl 4-{[(2S)-Oxiran-2-yl]methoxy}benzeneacetate ((S)-1; Table 2, Entry 8). [a]2D9 ¼ þ2.9 (c ¼ 1,
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CHCl3). H-NMR (400 MHz, CDCl3): 0.88 (t, J ¼ 7.2, 3 H); 1.31 (q, J ¼ 7.6, 2 H); 1.58 (q, J ¼ 8, 2 H);
2.73 – 2.90 (m, 2 H); 3.10 – 3.20 (m, 1 H); 3.54 (s, 2 H); 3.93 (q, J ¼ 5.2, 1 H); 4.09 (t, J ¼ 6.8, 2 H); 4.17–
4.21 (m, 2 H); 6.76 (d, J ¼ 8.8, 2 H); 7.10 (d, J ¼ 8.4, 2 H). 13C-NMR (400 MHz, CDCl3): 13.3; 18.7; 30.2;
40.0; 50.9; 64.2; 68.5; 114.3; 126.6; 129.9; 157.2; 173.1.
Butyl 4-{(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy}benzeneacetate (5). [a]2D9 ¼ þ36 (c ¼
1
0.5, MeOH). IR (KBr): 3290, 3210, 1724. H-NMR (400 MHz, CDCl3): 0.96 (t, J ¼ 7.6, 3 H); 1.08 (d,
J ¼ 6.4, 6 H); 1.31 – 1.60 (m, 4 H); 2.4 (s, 2 H); 2.79 – 2.86 (m, 3 H); 3.53 (s, 2 H); 3.96 – 4.09 (m, 5 H);
6.85 (d, J ¼ 8.8, 2 H); 7.17 (d, J ¼ 8.8, 2 H). 13C-NMR (400 MHz, CDCl3): 13.6; 19.0; 30.6; 48.9; 49.2;
64.6; 68.4; 70.5; 114.6; 126.6; 130.2; 157.7; 171.9.
Methyl 4-{[(2S)-Oxiran-2-yl]methoxy}benzeneacetate ((S)-4; Table 2, Entry 17). [a]2D9 ¼ þ10.5 (c ¼
1, MeOH) ([4]: [a]2D1 ¼ þ5.7( c ¼ 1, CHCl3)). IR (neat): 3000, 2949, 1738. 1H-NMR (400 MHz, CDCl3):
2.71 – 2.73 (m, 1 H); 2.86 – 2.88 (m, 1 H); 3.30 ꢀ 3.33 (m, 1 H); 3.55 (s, 2 H); 3.66 (s, 3 H); 3.89 (q, J ¼ 8,
1 H); 4.18 (dd, J ¼ 11.2, 2.8, 1 H); 6.85 (d, J ¼ 8, 2 H); 7.15 (d, J ¼ 8, 2 H). 13C-NMR (400 MHz, CDCl3):
40.1; 44.5; 50.0; 51.8; 68.6; 114.5; 126.4; 130; 157.3; 171.9.
Ethyl 4-{[(2S)-Oxiran-2-yl]methoxy}benzeneacetate ((S)-3; Table 2, Entry 13). [a]2D9 ¼ þ36.0 (c ¼ 1,
MeOH). IR (neat): 2982, 2929, 1735. 1H-NMR (400 MHz, CDCl3): 1.25 (t, J ¼ 1.2, 3 H); 2.70 – 2.80 (m,
1 H); 2.84 – 2.90 (m, 1 H); 3.30 (q, J ¼ 6, 1 H); 3.54 (s, 2 H); 3.93 (q, J ¼ 5.6, 1 H); 4.14 (q, J ¼ 7 , 2 H);
4.20 (dd, J ¼ 12, 4.4, 1 H); 6.86 (d, J ¼ 7.2, 2 H); 7.18 (d, J ¼ 6.8, 2 H). 13C-NMR (400 MHz, CDCl3):
14.1; 40.3; 44.5; 50.0; 60.7; 68.6; 114.5; 126.5; 130.0; 157.2; 171.6.