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Please use this identifier to cite or link to this item: 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

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