Conversion of methoxy vinyl ethers into glyoxal ketals

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dc.contributor.advisorCiufolini, Marco A.en_US
dc.creatorDilzer, Kirsten Franceen_US
dc.date.accessioned2009-06-03T23:55:12Zen_US
dc.date.available2009-06-03T23:55:12Zen_US
dc.date.issued1996en_US
dc.description.abstractA technique for the elaboration of ene products derived from aldehydes and 2-methoxypropene into glyoxal monoketals 5 has been devised, and some reactions of the resulting aldehydes have been examined. This methodology should resolve some difficulties encountered in the course of an ongoing total synthesis of phyllanthocin. Key phases of the present study involve oxidation of ether 1, readily available from butyraldehyde through a novel ene-type reaction discovered in our laboratory, using mCPBA and methanol to give a cyclic ketal 2. The resulting seven-membered ring was opened by ketal exchange with 1,3-propanethiol to give thioketal diol 3. Benzylation of the diol proceeded with complete selectivity for the primary alcohol, permitting differentiation of the diol functionality. Protection of the secondary alcohol as a MOM derivative and subsequent ketal exchange with bis(trifluoroacetoxy)iodobenzene reinstated the dimethoxy ketal. Debenzylation under Birch conditions released the free primary alcohol 4, Swern oxidation of which yielded the desired aldehyde 5.* ftn*Please refer to the dissertation for diagrams.en_US
dc.format.extent70 p.en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.callnoTHESIS CHEM. 1996 DILZERen_US
dc.identifier.citationDilzer, Kirsten France. "Conversion of methoxy vinyl ethers into glyoxal ketals." (1996) Master’s Thesis, Rice University. <a href="https://hdl.handle.net/1911/14042">https://hdl.handle.net/1911/14042</a>.en_US
dc.identifier.urihttps://hdl.handle.net/1911/14042en_US
dc.language.isoengen_US
dc.rightsCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.en_US
dc.subjectOrganic chemistryen_US
dc.titleConversion of methoxy vinyl ethers into glyoxal ketalsen_US
dc.typeThesisen_US
dc.type.materialTexten_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineNatural Sciencesen_US
thesis.degree.grantorRice Universityen_US
thesis.degree.levelMastersen_US
thesis.degree.nameMaster of Artsen_US
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