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- W2949403313 abstract "Abstract The magnesium bromide-diethyl etherate-catalyzed ring-opening of (3-(naphthalen-2-yl)-2,2-bis(trimethylsilyl)oxiran 2 with thiophenols affords (1-trimethylsilylvinyl)sulfides 3 and the (1-bromovinyl)silane 4 . Nucleophilic attack occurs regioselectively at the position α - to silicon. The compound 2 has been converted into the (1-trimethylsilylvinyl)amide 5 with an excess of acetonitrile and into the (1-trimethylsilylvinyl)acetate 6 with acetic acid/acetic anhydride. These reactions proceed with catalytic amounts of boron trifluoride-diethylether. Treatment of 2 with acetic acid alone gives naphthaldehyde. The epoxide 2 reacts also with MgBr 2 ·OEt 2 , MeLi/CuI, HX (X Br or Cl) and LiAlH 4 with nucleophilic attack at the bis(trimethylsilyl)-substituted carbon." @default.
- W2949403313 created "2019-06-27" @default.
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- W2949403313 date "2011-05-01" @default.
- W2949403313 modified "2023-09-25" @default.
- W2949403313 title "Acid-catalyzed reactions of (3-(naphthalen-2-yl)-2,2-bis(trimethylsilyl)oxiran. A new synthesis of functional-group-substituted vinylsilanes" @default.
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- W2949403313 doi "https://doi.org/10.1016/j.jorganchem.2011.02.024" @default.
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