Abstract A series of new 10, 11-dihydro-5H-dibenzo [b, f] silepins are prepared from the reaction o, o′-dilithiobibenzyl with the chlorosilanes HSiCl 3, ClCH 2 CH 2 CH 2 SiCl 3, MeSiHCl 2 and MeSi (CH 2 CH 2 CH 2 Br) Cl 2. The only isolated silepin product produced from HSiCl 3 is the spiro derivative. The silepin product produced from MeSiHCl 2 reacts with N, N-dimethylallylamine in the presence of H 2 PtCl 6 to give silipramine, a tricyclic ...