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Synthesis 1985; 1985(10): 977-979
DOI: 10.1055/s-1985-31412
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Lithium or Bromomagnesium 1,4- and 1,5-Dilithioalkan-2-yloxides: Preparation and Synthetic Applications

José Barluenga* , José R. Fernandez, Miguel Yus
  • *Departamento de Química, Orgánica, Facultad de Química, Universidad de Oviedo, Oviedo, Spain
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Publication Date:
27 September 2002 (online)

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Treatment of chloromethyl 2- or 3-chloroalkyl carbinols with butyllithium and then lithium naphthalenide or with ethylmagnesium bromide and then powdered lithium leads to the formation of lithium or bromomagnesium dilithioalkoxides, respectively, which represent trianionic species. The bromomagnesium 1,ω-dilithio-2-alkoxides undergo immediate elimination of lithium bromide and magnesium oxide to give ω-lithio-1-alkenes. These latter organometallic compounds as well as the lithium dilithioalkoxides react with various electrophiles to ,afford functionalized compounds.