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Studies related to the Westphalen rearrangement

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thesis
posted on 08.11.2018, 12:51 by John G.L. Jones
The reaction of four 3β-hydroxy-derivatives of Westphalen's diol with lead tetraacetate is described. The major products are the ethers 6β-acetoxy-3β,5-oxaethano-19-nor-5β-cholest-9(10)-ene (11(5]), 6β-acetoxy-9α,10-epoxy-3β,5-oxaethano-19-nor-5β,10α-cholestane, 6β-acetoxy-9β,10-epoxy-3β,5-oxaethano-19-nor-5β, 9β-cholestane and 6β-acetoxy-14-methyl-3β,5-oxa-ethano-18,19-bisnor-5β,8α,9β,10α,14β-cholest-13(17)-ene in which the original 5β-methyl group has been functionalised. Oxidation of (11[5]) with chromic acid gave products of attack at the 9,10-double bond and/or the allylic position 11. The reduction of (11[5)) and subsequent oxidation and boron-trifluoride catalysed cleavage of the tetrahydrofuran ring is described. [Continues.]

Funding

Science Research Council.

History

School

  • Science

Department

  • Chemistry

Publisher

© John Gareth Lloyd Jones

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

1970

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of the degree of Doctor of Philosophy at Loughborough University.

Language

en

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