Tributylstannane → Stannane, tributyl-1-cyclohexen-1-yl-

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Reaction Steps

To a solution of 1,3-cyclohexadiene (0.96 g, 12 mmol, d=0.84, 1143 uL) and Pd(PPh3)4 (462.2 mg, 0.4 mmol) in benzene (10 mL) under nitrogen atmosphere, was added Bu3SnH (1.16 g, 4 mmol, d=1.098, 1.06 mL) dropwise at room temperature and stirred for 15 minutes. After the solvent was removed on rotavap, the product was purified on silica flash chromatography (column 1.5 cm ID×20 cm) using a solvent gradient of 10:0 (100 mL) to 19:1(100 mL) to 9:1 (100 mL) of hexanes/EtOAc to afford cyclohexenyltributyltin (3.5 g, 9.4 mmol, 78.6% yield) as a clear liquid. Cyclohexenyltributyltin was characterized by 1H-NMR (CDCl3, 500 MHz). See FIG. 51.

Provenance & Evidence