Cleavage of C-O and C-H bonds in ethers by a genuine Si[double bond, length as m-dash]O bond.

Abstract

An isolable three-coordinate dialkylsilanone without substantial electronic stabilization reacts with several ethers resulting in the cleavage of the C-O or C-H and C-O bonds in the ethers which have not been observed for the hitherto-known electronically stabilised isolable Si[double bond, length as m-dash]O species. The formation of the Lewis base (DMAP and MTHP) complexes of the dialkylsilanone and the DFT calculations elucidated that the coordination of the ethereal oxygen atom to the Lewis acidic Si atom of the genuine Si[double bond, length as m-dash]O bond is a key interaction for the reaction.