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- Title
Tautomerism in Bis(oxazoline)s.
- Authors
Walli, Adam; Dechert, Sebastian; Meyer, Franc
- Abstract
Bis(oxazoline)s (BOXs) are a privileged ligand class and have found widespread use in catalysis. Herein, the tautomerism of selected BOX ligands was evidenced by X-ray diffractometry as well as by NMR and IR spectroscopy and supported by DFT calculations. In CDCl3 solution at room temperature, the new 1,1-bis(4,4-dimethyl-1,3-oxazolin-2-yl)-1-phenylmethane (Ph,HBOX-Me2) ligand is present as a 1:1 mixture of the diimine and iminoenamine tautomers. Thermodynamic and kinetic data for the tautomeric equilibrium were determined, which allowed comparison with related bidentate ligand classes. The other BOXs studied, H,HBOX-Me2, Me,HBOX-Me2, and tBu,HBOX-Me2, are largely present in the diimine form under similar conditions. IR spectroscopy was identified as a valuable tool for detecting the presence of the iminoenamine form as a minor component.
- Subjects
TAUTOMERISM; OXAZOLINE; NUCLEAR magnetic resonance spectroscopy; LIGANDS (Chemistry); X-ray diffractometers
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 31, p7044
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301282