dc.contributor.advisor |
Davis, B.R. |
en |
dc.contributor.advisor |
moved 6/7/16 jd |
en |
dc.contributor.author |
Hinds, Mark Gavin |
en |
dc.date.accessioned |
2007-09-04T05:26:51Z |
en |
dc.date.available |
2007-09-04T05:26:51Z |
en |
dc.date.issued |
1986 |
en |
dc.identifier |
THESIS 87-012 |
en |
dc.identifier.citation |
Thesis (PhD--Chemistry)--University of Auckland, 1986 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/1717 |
en |
dc.description |
Full text is available to authenticated members of The University of Auckland only. |
en |
dc.description.abstract |
Synthesis and reduction of a number of 1,3-diketones is reported. 2,2-Dialkyl-1,3-diaryl-1,3-propanediones yield cyclopropane-trans-1,2-diyl diacetates upon treatment with amalgamated zinc powder and dry hydrogen chloride in diethyl ether containing acetyl chloride. 1-Ary1-2,2,3-trialkyl diketones yield a cyclopropanediyl diacetate and a β-acetoxy ketone. The mechanism of reduction is discussed.
Cyclopropane-1,2-diols undergo ring opening under acidic conditions to give α-hydroxy-ketones or enones in most cases. A mechanism is discussed in terms of a cyclopropyl cation for 1,2-diarylcyclopropane-1,2-diols while 1-alkyl-2- arylcyclopropane-1,2-diol ring cleavage is formulated in terms of the stability of the conjugate acid of the ketone formed.
Reduction of hydroxymethylene cycloalkanones give rearranged and unrearranged monoketones as well as products of deformylation. The intermediacy of α,β-unsaturated ketones is discussed.
Clemmensen reduction of several 1,4-diketones is reported and a mechanism for the production of the alcohols formed is given in terms of an anomeric effect.
Preparation and oxidation of three cyclopropenes is reported and parallels with the ring opening of cyclopropane-1,2-diols observed. |
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dc.language.iso |
en |
en |
dc.publisher |
ResearchSpace@Auckland |
en |
dc.relation.ispartof |
PhD Thesis - University of Auckland |
en |
dc.relation.isreferencedby |
UoA9910167914002091 |
en |
dc.rights |
Restricted Item. Available to authenticated members of The University of Auckland. |
en |
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.title |
Studies in Clemmensen reduction and rearrangement |
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dc.type |
Thesis |
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thesis.degree.discipline |
Chemistry |
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thesis.degree.grantor |
The University of Auckland |
en |
thesis.degree.level |
Doctoral |
en |
thesis.degree.name |
PhD |
en |
dc.rights.holder |
Copyright: The author |
en |
dc.identifier.wikidata |
Q112847191 |
|