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46149087667
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Typical experimental procedure for synthesis of 6ab and 4ab A neat mixture of N-isopropytbenzylidene amine la (10 mmol, and ethyl cyanoacetate 2b (30 mmol, was allowed to stand at room temperature during 8 days. Addition of EtOH 95% has for consequence the crystallization of cyclohexene 6ab (56% yield of isolated pure product, Mp: 216°C. 1H -NMR (500 MHz, CDC13) δH, 0.68 (t, 3H, J 7.1, 1.06 (t, 3H, J 7.1, 3.73 (qm, 2H, J 7.1, 4.00 (d, HA, J 12.1, 4.07 (qm, 2H, J 7.1, 4.18 (dd, H B, J 12.1, J 2.3, 4.49 (d, HC, J 2.3, 5.04 (s, 2H, NH2, 7.25-7.48 (m, 10H arom, δC (125 MHz, CDC13) 13.29 and 13.35 (qm, CO2CH2CH3, J 127.6, 47.90 (dm, C3-HA, J 132.0, 48.34 (dm, C6-HC, J 138, 49.23 (dm, C2-HB, J 138, 57.86 t, C
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3) 1.42 (t, 3H, J 7.1), 4.41 (q, 2H, J 7.1), 7.30-8.03 (5 H arom), 8.27 (s, 1H).
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15
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46149096645
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Crystal data for 6ab: C26H25 N3O4, Mr= 443.49, monoclinic, P21/c, a= 7.642(4, b, 19.999(6, c, 15.643(5) Å, b, 93.71(4)°, V, 2386(, Å-3, Z, 4, Dx, 1.235 Mg.m-3, λ(MoKα, 0.71073Å, μ, 0.84 cm-1, F(000, 936, T, 293 K. Sample (0.45*0.38*0.33 mm) studied on CAD4 NONIUS (MoKα, Range HKL, H 0,9 K 0,25 L -19,19, 5580 unique reflections (3027 with 1>2.0σ(I, Structure solved with SIR-97 (Altomare & al, 1998) and refined with SHELXL97 (Sheldrick, 1997) by the full-matrix least-square techniques (use of F square magnitude; x, y, z, βij for C, 0Oand N atoms, x, y, z in riding mode for H atoms; 299 variables and 3027 observations with 1>2.0δ(I, calc w=1/[(σ2(Fo)2+(0.0596p)2+0.2596P] where p=(Fo2+2Fc2)/3 with the resulting R, 0.045, RW, 0.109 and S
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W= 1.013(residual Ap ≤ 0. 18 e.Å-3) Crystallographic date: have been deposited at the Cambridge Crystallographic Data Centre under the number CCDC 220602 and may be obtained free of charge from the Director(depositγcdc. cam. ac.uk).
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