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http://hdl.handle.net/11375/11357
Title: | Reactions of Phthalide Ortho Esters with Dienophiles: Synthesis of Naphthalenes and Homoquinones |
Authors: | Contreras, Luis |
Advisor: | MacLean, D. B. |
Department: | Chemistry |
Keywords: | Chemistry;Chemistry |
Publication Date: | May-1980 |
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> |
URI: | http://hdl.handle.net/11375/11357 |
Identifier: | opendissertations/633 1966 1095810 |
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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