Reactivity of hypervalent species of silicon: cleavage of the allyl-silicon bond

Article abstract of DOI:10.1016/0022-328X(87)80257-7

The reactivities of the silicon-allyl bonds in two kinds of pentacoordinated silicon species CH2=CHCH2Si(o-O2C6H4)2^-NMe4⁺ (1) and CH2=CHCH2Si(OCH2CH2)3N (2) has been compared.In the allyl transfer to carbonyl compounds under nucleophilic conditions (NaOMe, KF or Bu4NF) and electrophilic conditions (TiCl4, AlCl3, BF3) these two species show quite different behaviour.Complex 1 is activated by nucleophiles, while for 2 transfer occurs under electrophilic conditions.These results indicate that the reactivity of these species is a function of their overall charge and geometry.