Nucleophilic Attack of R-lithium at Tetrahedral Silicon in Alkoxysilanes. An Alternate Mechanism

Richard Laine

Joseph C Furgal and Richard M Laine (2016)

Bulletin of the Chemical Society of Japan(0).

The currently accepted mechanism for nucleophilic attack at silicon in tetraalkoxysilanes, eg Si (OEt) 4 is suggested to involve formation of penta-and then hexacoordinated intermediates as supported by the apparent exclusive formation of R 3 SiOR'and R 4 Si from nucleophilic attack by RLi and RMgX. Our recent discovery of a direct route from biogenic silica to tetraalkoxy-spirosiloxanes prompted us to revisit this reaction as a potential route to diverse silicon containing species with single Si-C bonds as early studies demonstrate...