A series of new 10,11-dihydro-5H-dibenzo[b,f]silepins are prepared from the reaction o,o′-dilithiobibenzyl with the chlorosilanes HSiCl3, ClCH2CH2CH2SiCl3, MeSiHCl2 and MeSi(CH2CH2CH2Br)Cl2. The only isolated silepin product produced from HSiCl3 is the spiro derivative. The silepin product produced from MeSiHCl2 reacts with N,N-dimethylallylamine in the presence of H2PtCl6 to give silipramine, a tricyclic