Thesis-1996-Walton.pdf (3.03 MB)
Epoxidation using dioxiranes
thesis
posted on 2012-09-27, 12:00 authored by Lesley WaltonChapter 1 contains a brief review of the historical background of dioxiranes
and an outline of their more recent chemistry.
The preparation of homochiral 2-fluoro-2-substituted-1-tetralones and ethyl
2-fluoro-1-indanone-2-carboxylate is described in Chapter 2 and the X-ray
crystal structure of (1' R,2' R,5' R)-( -)-menthyl 2S-fluoro-1-tetralone-2-
carboxylate presented. The synthesis of racemic 2,5,7 -trifluoro-1-indanone-2-
carboxylate is also discussed. The dioxirane derivatives of the above ketones have been prepared in situ
and have been shown to epoxidise trans-stilbene, trans-β-methylstyrene and
6-chloro-2,2-dimethyl-2H-1-benzopyran, but not enantioselectively. The
individual results of these epoxidations are given in Chapter 3. The
incorporation of fluorine into the aromatic ring of aryl alkyl ketones is shown to
increase dioxirane reactivity. Chapter 4 briefly describes the reactions carried out in order to ascertain the
optimum conditions for the epoxidation of alkenes by in situ derived
dioxiranes. The rate of this oxidation was shown to be highly dependent on
the concentration of the dioxirane in the organic phase.
Described in Chapter 5 are the procedures used for the isolation of the
dioxirane derivatives of dimethyldioxirane, 1,1, 1-trifluoroacetone, 2,2,2-
trifluoroacetophenone, hexafluoroacetone and cyclohexanone, in solutions of
the corresponding ketone with or without dichloromethane.
History
School
- Science
Department
- Chemistry
Publisher
© L. WaltonPublication date
1996Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.Language
- en