38458-30-9Relevant articles and documents
Catalyst-free Diels-Alder reactions of vinylphosphonates with cyclopentadienones
Benmeddah, Amel,Villemin, Didier,Mostefa-Kara, Bachir,Bar, Nathalie,Legay, Remi
, p. 871 - 879 (2017)
The unprecedented thermal Diels-Alder reaction of the diethyl vinylphosphonate and diethyl styrylphosphonate with various cyclopentadienones is described. In these Diels-Alder reactions, catalysis was not required and the corresponding cycloadducts deriva
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 (2008/02/02)
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.