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http://hdl.handle.net/11375/11357
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DC Field | Value | Language |
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dc.contributor.advisor | MacLean, D. B. | en_US |
dc.contributor.author | Contreras, Luis | en_US |
dc.date.accessioned | 2014-06-18T16:54:24Z | - |
dc.date.available | 2014-06-18T16:54:24Z | - |
dc.date.created | 2009-12-21 | en_US |
dc.date.issued | 1980-05 | en_US |
dc.identifier.other | opendissertations/633 | en_US |
dc.identifier.other | 1966 | en_US |
dc.identifier.other | 1095810 | en_US |
dc.identifier.uri | http://hdl.handle.net/11375/11357 | - |
dc.description.abstract | <p>A new reaction between phthalide ortho esters with a series of dienophiles has been studied. It was found that treatment of 1,1-diethoxyphthalan or 5,6-dimethoxy-1,1-diethoxyphthalan with activated acetylenes yielded tetrasubstituted naphthalenes. Reaction of 1,1-diethoxyphthalan with diethyl maleate afforded a mixture of enol ethers and a trisubstituted naphthalene. The enol ethers were converted into a disubstituted naphthol under acidic conditions. Treatment of phthalide ortho esters with 1,4-benzoquinone or 1,4-napththoquinone gave p-homoquinones instead of the expected linear tricyclic and tetracyclic aromatic compounds.</p> <p>The formation of the compounds derived from the reaction of phthalide ortho esters with dienophiles has been rationalized in terms of a mechanism that involves l-ethoxyisobenzofurans as intermediates.</p> | en_US |
dc.subject | Chemistry | en_US |
dc.subject | Chemistry | en_US |
dc.title | Reactions of Phthalide Ortho Esters with Dienophiles: Synthesis of Naphthalenes and Homoquinones | en_US |
dc.type | thesis | en_US |
dc.contributor.department | Chemistry | en_US |
dc.description.degree | Doctor of Philosophy (PhD) | en_US |
Appears in Collections: | Open Access Dissertations and Theses |
Files in This Item:
File | Size | Format | |
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fulltext.pdf | 2.24 MB | Adobe PDF | View/Open |
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