1309645-99-5Relevant academic research and scientific papers
Acid-catalyzed reactions of (3-(naphthalen-2-yl)-2,2-bis(trimethylsilyl) oxiran. A new synthesis of functional-group-substituted vinylsilanes
Safa, Kazem D.,Behmagham, Farnaz,Ghorbanpour, Khatereh
, p. 1840 - 1844 (2011)
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 MgBr2·OEt 2, MeLi/CuI, HX (XBr or Cl) and LiAlH4 with nucleophilic attack at the bis(trimethylsilyl)-substituted carbon.
