Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

Abstract

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.

https://doi.org/10.1071/CH9850111

© CSIRO 1985


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