The unusual reaction of [8-(dimethylamino)methyl-1-naphthyl]phenylchlorosilane with fluoren-9-yllithium. Synthesis of kinetically stable dibenzosilafulvene

The first stable dibenzosilafulvene, 14-[8’-(dimethylamino)metliyl-l’-naplitliyl]-14-plienyl-14-silafluorenylide 1, was obtained in one step from fluoren-9-yllithium and [8-(dimethylamino)methyl-l-naphthyl]phenylchlorosilane 2 as a stable solvate with THF; the zwitterionic structure of 1 is established by ¹H, ¹³C and ²⁹Si NMR in solution and solid state and its reactions with crotonaldehyde, ethanol and triethylethylidene-λ⁵-phosphane are described.