Journal Article
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, GD; Edwards-Davis, D; Field, LD; Masters, AF; Maschmeyer, T; Ward, AJ; Buys, IE; Turner, P; ,
Australian Journal of Chemistry
ISSN: 0004-9425
EISSN: 1445-0038
CSIRO PUBLISHING
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-dibenzoyl-phenanthrene) 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 H2PO4. Compounds 7, 8, 9-Cl, 9-Br, and 10 have been structurally characterized using X-ray crystallography.