Title page for ETD etd-7897-122632

Type of Document Master's Thesis
Author Clevenger, Margo
Author's Email Address waygo@gbsias.com
URN etd-7897-122632
Title Synthetic Routes to 3-Fold Symmetric Tridentate Oxygen Donor Ligands
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Anderson, Mark R.
Merola, Joseph S.
Hanson, Brian E. Committee Chair
  • organometallics
  • phosphite synthesis
  • Oxygen donor ligands
  • tridentate ligands
  • anionic liigands
Date of Defense 1997-08-01
Availability unrestricted
The class of ligands represented by [CpCo(P(O)(OR)2)3]-, L- , were first synthesized by W. Kläui in 1977. These ligands have been found to coordinate to a variety of low and high oxidation state metals through the use of its three P=O oxygen atoms as donors. The ligands act as mono-anionic six electron donors which make them similar to the more widely known cyclopentadienyl ligands, (C5H5-xRx)-, but have electronic properties like those of fluoride or oxide. Also, it has been found that the coordination chemistry of L- resembles the unsubstituted tris(pryrazolyl)hydroborato six electron ligand, (RB(pz)3)-. All three of these ligands can be modified by changing the substituent R. The Kläui ligand offers a good opportunity to synthesize a chiral derivative.

In the process to obtain the chiral version, (cyclopentadienyl)tris(biphenyl-phosphito-P)cobaltate(1-), 18, was synthesized from 2,2'-biphenol. This was characterized through NMR, mass spectroscopy, and XPS. Next, a racemic version, (cyclopentadienyl)tris(biphenylphosphito-P)cobaltate(1-), 17, was synthesized from (±)1,1’-bi-2-naphthol. A one-pot synthesis for the rac-binaphthyl phosphite derivative was developed with an increased yield from the previously published synthesis. The racemic version of the ligand was characterized by NMR and mass spectroscopy. The chiral version has not yet been synthesized, however, by following the developed procedure for the non-chiral version, the ligand could be synthesized from optically active 1,1'-bi-2-naphthol.

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