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2nd September 2013 @ 13:26

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Reaction information

*#Reaction file  
*Reaction file type CDX

To a stirred solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) in dry THF (5.0 mL) under argon at –80 °C, nBuLi (0.8 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise and left for 10 minutes.  N-Allyl-N-methyl-N-[(Z)-3-phenyl-2-propenyl]amine (558, 188 mg, 1.0 mmol) as a solution in THF (2.0 mL) was added dropwise, warmed to room temperature, stirred for 7 hrs before quenching with methanol (5.0 mL) and a saturated solution of NaHCO3 (8.0 mL).  The product was extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a pale oil (150 mg, 0.79 mmol, 79 %).

*Yield (%)  79
*Type of Yield Isolated product yield
DM Thesis_2000_pp81-89.pdf
DM Thesis_2000_pp176.pdf
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Attached Files
DM Thesis_2000_pp176.pdf
DM Thesis_2000_pp81-89.pdf