From Carbanions to Organometallic Compounds: Quantification of Metal Ion Effects on Nucleophilic Reactivities

Angew. Chem. Int. Ed. 2015, 54, 12497-12500, Angew.Chem.Int.Ed.

Angew. Chem. 2015, 127, 12676-12680, Angew.Chem.

The influence of the metal on the nucleophilic reactivities of indenyl metal compounds was quantitatively determined by kinetic investigations of their reactions with benzhydrylium ions (Ar2CH+) and structurally related quinone methides. With the correlation equation log k2=sN(N+E), it can be derived that the ionic indenyl alkali compounds are 1018 to 1024 times more reactive (depending on the reference electrophile) than the corresponding indenyltrimethylsilane.

TU München