ORGANIC-CARBON, NITROGEN OR OXYGEN-CENTERED ANIONS CAN DISPLAY ELECTROPHILIC REACTIVITY

Carbanions bearing a leaving group in the alpha position can react as electrophiles. They couple with organolithium or Grignard reagents to give a new organometallic compound. The iteration of the process, whic h would generally lead to a scenes of homologous products, is circumve nted if the organometallic formed can undergo a fast intramolecular re action. Accordingly, various alkenes, including vinylic halides, enol ethers or thioethers could be easily and efficiently obtained. This el ectrophilic behaviour of anionic species is not limited to carbanions; examples of electrophilic amination or hydroxylation based on this un expected reactivity are also reported.