Synthesis p. 977 - 979 (1985)
Update date:2022-08-10
Topics:
Barluenga, Jose
Fernandez, Jose R.
Yus, Miguel
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 dilithiothioalkoxides, 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 dithioalkoxides react with various electrophiles to afford functionalized compounds.
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