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dc.degree.departmentChemistryen_US
dc.rights.availabilityUnrestricted.
dc.creatorPark, Gyoosoon
dc.date.accessioned2016-11-14T23:09:46Z
dc.date.available2011-02-18T23:55:21Z
dc.date.available2016-11-14T23:09:46Z
dc.date.issued1988-12
dc.identifier.urihttp://hdl.handle.net/2346/20774en_US
dc.description.abstractMy research objective was to investigate two-step intramolecular nucleometallationcoupling reactions of allenes to form polyfiinctional heterocyclic molecules. This reaction sequence takes place by either: a) an intramolecular oxy- or aminomercuration of an allene followed by a transmetallation of the mercury by palladium(II), then a coupling reaction (e.g., with carbon monoxide and an alcohol to form estCTs); or b) an intramolecular oxy- or aminopalladation of an allene followed, in situ, by the coupling. The results of this investigation have led to: 1) the development of a stereospecific approach to cis-2-15-alkyltetrahydrofiiran-2-yl)-2-propenoates; 2) the discovery of a stereospecific reduction of cis-2-(5-alkyltetrahydrofuran-2-yl)-2-propenoates; and 3) the development of a general synthetic approach to natural and unnatural nonactic acid esters. Scheme 1 represents our basic idea for the intramolecular nucleometallation of allenes (1) using mercury or palladium salts. A metal-complexed allene (2) should cyclize to form an intermediate a-vinyl complex of the metal (3). The complex 3 (where M = palladium) can undergo carbonylation and alkoxide coupling in the presence of carbon monoxide and an alcohol to form substituted acrylate esters (4) which should be valuable intermediates for organic synthesis.
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherTexas Tech Universityen_US
dc.subjectOrganic compounds -- Synthesisen_US
dc.subjectPalladium catalystsen_US
dc.subjectTetrahydrofuran -- Synthesisen_US
dc.subjectAllene -- Synthesisen_US
dc.titleStereoselective syntheses of functionalized tetrahydrofurans via intramolecular oxymetallations of allenes and syntheses of methyl nonactate homologues
dc.typeDissertation


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