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Mechanisms of the Intriguing Rearrangements of Activated Organic Species

Harman, David Grant

Description

The β-acyloxyalkyl radical rearrangement has been known since 1967 but its mechanism is still not fully understood, despite considerable investigation. Since the migration of a β-trifluoroacetoxy group generally proceeds more rapidly and with more varied regiochemistry than its less electronegative counterparts, this reaction was studied in the hope of understanding more about the subtleties of the mechanism of the β- acyloxyalkyl radical rearrangement. The mechanism of the catalysed...[Show more]

dc.contributor.authorHarman, David Grant
dc.date.accessioned2008-06-23T01:22:24Z
dc.date.accessioned2011-01-04T02:38:52Z
dc.date.available2008-06-23T01:22:24Z
dc.date.available2011-01-04T02:38:52Z
dc.identifier.otherb21933972
dc.identifier.urihttp://hdl.handle.net/1885/47123
dc.description.abstractThe β-acyloxyalkyl radical rearrangement has been known since 1967 but its mechanism is still not fully understood, despite considerable investigation. Since the migration of a β-trifluoroacetoxy group generally proceeds more rapidly and with more varied regiochemistry than its less electronegative counterparts, this reaction was studied in the hope of understanding more about the subtleties of the mechanism of the β- acyloxyalkyl radical rearrangement. The mechanism of the catalysed rearrangement of Nalkoxy- 2(1H)-pyridinethiones was also explored because preliminary studies indicated that the transition state (TS) for this process was isoelectronic with TSs postulated for the β-acyloxyalkyl radical and other novel rearrangements. ¶ ...
dc.language.isoen
dc.rights.uriThe Australian National University
dc.subjectβ-acyloxyalkyl
dc.subjectradical rearrangement
dc.subjectNalkoxy- 2(1H)-pyridinethiones
dc.subjectβ-trifluoroacetoxy
dc.subjectregiochemistry
dc.subjectcatalysed rearrangement
dc.subjecttransition state (TS)
dc.titleMechanisms of the Intriguing Rearrangements of Activated Organic Species
dc.typeThesis (PhD)
dcterms.valid2003
local.description.refereedyes
local.type.degreeDoctor of Philosophy (PhD)
dc.date.issued2003
local.contributor.affiliationFaculty of Science, Department of Chemistry
local.contributor.affiliationThe Australian National University
local.identifier.doi10.25911/5d7a29ed7c4e9
local.mintdoimint
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