An improved method for the synthesis of pentaphenylcyclopentadiene is
suggested. It involves the reaction of tetraphenylcyclopentadienone wi
th PhMgBr and subsequent treatment of the reaction mixture with an exc
ess of LiAlH4 in THF. The effect of arylating agents and reducing agen
ts on the yield of the target product is studied. The method suggested
can be used for synthesizing other polyaromatic cyclopentadienes, in
particular, 2,5-triphenyl-3,4-(1,8-naphthylene)cyclopentadien.