41442-14-2Relevant academic research and scientific papers
Fused supracyclopentadienyl ligand precursors. synthesis, structure, and some reactions of 1,3-diphenylcyclopenta[l]phenanthrene-2-one, 1,2,3-Triphenylcyclopenta[l]phenanthrene-2-ol, 1-Chloro-1,2,3-triphenylcyclopenta[l]phenanthrene, 1-Bromo-1,2,3-triphenylcyclopenta[l]phenanthrene, and 1,2,3-Triphenyl-1H-cyclopenta[l]phenanthrene
Dennis, Glen D.,Edwards-Davis, David,Field, Leslie D.,Masters, Anthony F.,Maschmeyer, Thomas,Ward, Antony J.,Buys, Irmi E.,Turner, Peter
, p. 135 - 146 (2006)
The photochemical reaction of 1,3-diphenylcyclopenta[l]phenanthrene-2-one 5 (phencyclone) with oxygen in acetone leads to the formation of 1,2,3-trihydro-1,2,3-triphenylcyclo-penta[l]phenanthrene 7 (9,10-dibenzoylphenanthrene) along with a trace of the lactone 1,4-diphenylcyclo-3-pyran[l]phenanthrene-2-one 8. An independent synthesis of 8 was achieved by the reaction of 5 with FeCl3 in CHCl3. The treatment of 5 with phenyllithium yields 1,2,3-triphenylcyclopenta[l]phenanthrene-2-ol 9-OH in good yield. Subsequent reaction of 9-OH with SOCl2 or SOBr2 in pyridine leads to the formation of the halo-analogues 1-chloro-1,2,3-triphenylcyclopenta[l]phenanthrene 9-Cl and 1-bromo-1,2,3-triphenylcyclopenta[l]phenanthrene 9-Br, respectively. Treatment of 9-OH with HBr in acetic acid affords the rearranged product 1,1,3-triphenylcyclopenta[l]phenanthrene-2-one 10 with a trace of 9-Br. Treatment of 9-Cl or 9-Br with zinc in acetic acid affords 1,2,3-tri-phenyl-1H-cyclopenta[l]phenanthrene 9-H. 9,10-Phenanthrenediylbis(phenyl)methanone 7 is formed in good yield upon treatment of 9-OH with HI in acetic acid followed by heating with H 2PO4. Compounds 7, 8, 9-Cl, 9-Br, and 10 have been structurally characterized using X-ray crystallography. CSIRO 2006.
Improved method for the synthesis of pentaphenylcyclopentadiene
Dyumaev, V. K.,Davydov, D. V.,Beletskaya, I. P.
, p. 571 - 573 (2007/10/02)
An improved method for the synthesis of pentaphenylcyclopentadiene is suggested.It involves the reaction of tetraphenylcyclopentadienone with PhMgBr and subsequent treatment of the reaction mixture with an excess of LiAlH4 in THF.The effect of arylating agents and reducing agents on the yield of the target product is studied.The method suggested can be used for synthesizing other polyaromatic cyclopentadienes, in particular, 1,2,5-triphenyl-3,4-(1,8-naphthylene)cyclopentadiene.
