Abstract
(1-Halo-2-propenyl)trimethylsilanes underwent the addition of polyhalides or α-haloesters under catalysis by the copper(I) ethanolamine or N ,N ,N ′,N ′-tetramethylethylenediamine complex to bring about vinylsilane derivatives through dehalogenation accompanying the migration of the carbon-carbon double bond.
Key words
addition reaction - silicon - copper catalysis - dehalogenation - carbon-carbon double bond
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General Procedure for the Reaction of α-Halogen Substituted Allylsilanes with Polyhalides : A solution comprising (1-bromo-2-propenyl)trimethylsilane (1b , 0.386 g, 2 mmol), a polyhalide (4 mmol), 2-aminoethanol (0.611 g, 10 mmol), CuCl (0.02 g, 0.2 mmol), and t -BuOH (5 mL) was stirred under reflux. The reaction mixture was then poured into H2 O and extracted with Et2 O. After the solvent was evaporated under reduced pressure, the product was isolated from the residue by preparative GC or column chromatography on silica gel. Compound 2a : a colorless oil. IR (neat): 3082, 1624 cm-1 . 1 H NMR (400 MHz, CDCl3 ): δ = 6.08 (dt, J = 18.6, J = 6.0, 1 H, CH2 -CH =CH), 5.96 (d, J = 18.6, 1 H, CH=CH -SiMe3 ), 3.42 (d, J = 6.0 Hz, 2 H, CH
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