Geminal Dianions Stabilized by Main Group Elements.

This review is dedicated to the chemistry of stable and isolable species that bear two lone pairs at the same C center, i.e., geminal dianions, stabilized by main group elements. Three cases can thus be considered: the geminal-dilithio derivative, for which the two substituents at C are neutral, the yldiide derivatives, for which one substituent is neutral while the other is charged, and finally the geminal bisylides, for which the two substituents are positively charged. In this review, the syntheses and electronic structures of the geminal dianions are presented, followed by the studies dedicated to their reactivity toward organic substrates and finally to their coordination chemistry and applications.