Knoevenagel condensation of the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione with 9-anthracenecarboxaldehyde: Synthesis of the second-generation ligand 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2006-11

AUTHORS

William H. Watson, Bhaskar Poola, Michael G. Richmond

ABSTRACT

The Knoevenangel condensation between 9-anthracenecarboxaldehyde and the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione (bpcd) takes place rapidly in CH2Cl2/MeOH solution in the presence of molecular sieves (4 Å) to produce the functionalized ligand 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione. The title compound has been isolated and characterized in solution by IR, NMR, and UV-vis spectroscopies, and the solid-state structure has been established by X-ray diffraction analysis. 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione crystallizes in the triclinic space group P−1, a=10.227(2) Å, b=13.865(2) Å, c=15.905(2) Å, α=112.157(2)°, β=101.424(2)°, γ=100.065(3)°, V=1968.5(5) Å3, Z=2, and dcalc=1.101 Mg/m3; R=0.0873, Rw=0.2604 for 7452 reflections with I>2σ(I). The cyclic voltammetric behavior for 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione has been studied, and the observed redox data and results from extended Hückel MO calculations are discussed relative to the parent ligand bpcd. More... »

PAGES

715-722

References to SciGraph publications

  • 2003-09. Regiospecific CO substitution in (μ-H)Ru3(μ3− η3-CHCHCMe)(CO)9 by 4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione(bpcd). X-ray structure of (μ-H)Ru3(μ3−η3-CHCHCMe)(CO)7(bpcd)⋅MeOH in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • 2003-10. Bridging and chelating diphosphine ligands in Ru3(μ-H)(μ-N=CPh2)(CO)8(P—P). X-ray diffraction structures of Ru3(μ-H)(μ-N=CPh2)(CO)8(dmpe) and Ru3(μ-H)(μ-N=CPh2)(CO)8(bpcd) in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • 2006-01. Synthesis, redox properties, and molecular structure of 4,5-diethylthio-4-cyclopenten-1,3-dione: Cyclic voltammetric evidence for a kinetically stable radical anion in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • 2004-08. Reaction of the dicobalt alkyne compound Co2(CO)6(μ-dmad) with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione (bpcd). Spectroscopic properties, X-ray diffraction data, and thermal reactivity of the chelating isomer of Co2(CO)4(bpcd)(μ-dmad) in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • 2004-10. New polydentate sulfide ligands: Synthesis, redox properties, and molecular structure of 4,5-bis(p-tolylthio)-4-cyclopenten-1,3-dione in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • 2001-08. CO Substitution in PhCCo3(CO)9 by 4,5-Bis(diphenylphosphino)-4-cyclopenten-1,3-dione (bpcd). Ligand Fluxionality, Kinetics, and X-Ray Structures of PhCCo3(CO)7(bpcd) and in STRUCTURAL CHEMISTRY
  • 2006-01. Chlorine-atom abstraction and cluster fragmentation in the reaction of H3Re3(CO)10(MeCN)2 with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione (bpcd): X-ray diffraction structure of fac-ClRe(CO)3(bpcd) in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
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