Title
Properties and separation method of enantiomers of the mono- and bis-substituted derivatives of 3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene: structural analysis using X-ray diffraction and circular dichroism
Author
Arkadiusz Kłys, Anna Makal, Anna Zdzienicka
Year
2016
Journal
Tetrahedron: Asymmetry
Abstract
This work expands on the recent separation of the enantiomers of the C2-symmetrical bis-substituted derivatives of 1,1′-diphosphaferrocene. The effective separation of mono-substituted 1,1′-diphosphaferrocenes by the proposed method is demonstrated. The absolute configuration of the three separated components was established using X-ray diffraction. Circular dichroism spectra were collected for all of the separated compounds. The spectrum of each compound shows a characteristic curve, and the curves for the enantiomers are symmetrical. We also show that the correct absolute configuration for similar species can be assigned on the basis of the obtained data. We propose an explanation for the abnormal 1H NMR spectra of phospholyl protons in some derivatives of 1,1′-diphosphaferrocene. A density functional theory (DFT) study of the conformation, as well as circular dichroism and NMR spectra of the chosen species, is also presented.
Instrument
J-815
Keywords
Circular dichroism, Absolute configuration