期刊
JOURNAL OF ORGANOMETALLIC CHEMISTRY
卷 696, 期 9, 页码 1840-1844出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2011.02.024
关键词
Bis(trimethylsilyl)epoxides; Vinylsilylsulfides; Peterson reaction; Vinylsilanes; Acid-catalyzed ring-opening
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 alpha- 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)center dot OEt(2), MeLi/CuI, HX (X=Br or Cl) and LiAlH(4) with nucleophilic attack at the bis(trimethylsilyl)-substituted carbon. (C) 2011 Elsevier B.V. All rights reserved.
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