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The ratio was determined by 1H NMR through integration of the two respective vinylic signals at δ 4.87 and 4.78 ppm and does not depend on the reaction conditions (base, temperature).
12.
It should be noted that in addition to these substantial deviations regarding yield, diastereoisomeric ratio and separability the NMR data of the minor isomer of compound 2 did not match the ones reported by Park et al. [8m].
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16.
The mixture is inseparable by means of gas chromatography, but nonetheless serves as an appropriate analytical standard. GC conditions: HP 6890N connected to MSD 5975B (Agilent) and MPS-2 autosampler (Gerstel). GC: HP-5ms column (Agilent) 30 m x 0.32 mm ID x 0.25 μm film; carrier gas: Helium 5.0 (const. flow 1.0 mL/min); injection: 1μL splitless, 250°C; oven program: 60°C (hold: 4 min) to 320°C (held: 4 min), heating rate: 10°C/min; transfer line: 330°C. MS: Ionization mode: electron impact (EI); scan-range m/z: 40–300.
17.
Ytterbium was activated by sequential washing with 0.5 M HCl, H2O, MeOH and Et2O followed by drying under reduced pressure.
