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Synthesis 1986; 1986(12): 1035-1037
DOI: 10.1055/s-1986-31864
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Nucleophilic Addition of Lithiated Phenyl Trimethylsilylmethyl Sulfide to Activated Olefins. A Facile Synthesis of 2-(Functionally) Substituted Silylcyclopropanes

Ernst Schaumann* , Carsten Friese, Carsten Spanka
  • *Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-2000 Hamburg 13, West Germany
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Publication Date:
12 September 2002 (online)

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The lithio derivative of phenyl trimethylsilylmethyl sulfide undergoes smooth addition to activated ethylene derivatives to afford trimethylsilylcyclopropanes, except for the addition to methyl 2-phenylpropenoate which leads to the formation of methyl 4-trimethylsilyl-2-phenyl-4-(phenylthio)butanoate.