Chemo-reductive silylation of hypersilyl arenes - Unusual cleavage of an aromatic CC double-bond

The novel silylated diene 3, a by-product from the reaction of PhSiCl3 with Me3SiCl and lithium in THF at low temperatures was isolated and its structure has been confirmed by X-ray crystallography. The formation of 3 formally arises from a consecutive chemo-reductive cleavage of the aromatic CC double bond in the phenyl-tris(trimethylsilyl)silane (1a) by action of lithium and trimethylchlorosilane.