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Article << Previous     |     Next >>   Contents Vol 38(1)

The Stereochemistry of Organmetallic Compounds. XXV. The Stereochemistry of Displacements of Secondary Methanesulfonate and p-Toluene-sulfonate esters by Diphenylphosphide Ions. X-ray Crystal Structure of (5α- Cholestan- 3α-yl)diphenylphosphine Oxide

Jackson W Roy, RJ Thomson and . Mackay.M.F

Australian Journal of Chemistry 38(1) 111 - 118
Published: 1985


Reactions of both axial and equatorial cholestan-3α- and -3β-yl mesylates and tosylates with sodium diarylphosphides give cholestanylphosphines in good yield and with complete inversion of stereochemistry. The stereochemistry has been established by an X-ray crystal structure of (5α-cholestan-3α-yl) diphenylphosphine oxide, and a general method for distinguishing between axial and equatorial phosphines based on 31P N.M.R . spectra is presented. The monophosphines were used as ligands in asymmetric hydrogenation, but only low optical yields were obtained.

Full text doi:10.1071/CH9850111

© CSIRO 1985

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