{"id":{"repo_id":"vt","oai_identifier":"oai:vtechworks.lib.vt.edu:10919/49858"},"canonical_url":"https://search.dev.ndltd.org/etd/vt/oai:vtechworks.lib.vt.edu:10919/49858","repository":{"repo_id":"vt","name":"Virginia Tech","base_url":"https://vtechworks.lib.vt.edu/oai/request"},"display":{"title":"Investigation of the synthesis and thermal rearrangements of 1,2,3,4,5-Pentaphenyl-2,4,-Cyclopentadiene Alkyl Ethers","abstract":"A comparative synthetic study of a series of six 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene alkyl ethers was investigated. It was determined that the most efficient route to these ethers was not the most generally accepted route to ethers - the Williamson Reaction - but rather a solvolysis reaction between 1-bromo-1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene and the appropriate alcohol. Thermal rearrangement of the ethers had been expected to rearrange by a [1,5]-sigmatropic shift of the phenyl group in the 1-position to yield the corresponding enol ether. However, this appeared to occur only as a trace in some cases. Rather, the major product of the thermal rearrangements of these ethers was actually the elimination product, the hydrocarbon, 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene. The elimination is most likely the result of a retro-ene reaction.","abstract_html":"A comparative synthetic study of a series of six 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene alkyl ethers was investigated. It was determined that the most efficient route to these ethers was not the most generally accepted route to ethers - the Williamson Reaction - but rather a solvolysis reaction between 1-bromo-1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene and the appropriate alcohol. Thermal rearrangement of the ethers had been expected to rearrange by a [1,5]-sigmatropic shift of the phenyl group in the 1-position to yield the corresponding enol ether. However, this appeared to occur only as a trace in some cases. Rather, the major product of the thermal rearrangements of these ethers was actually the elimination product, the hydrocarbon, 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene. The elimination is most likely the result of a retro-ene reaction.","abstract_has_math":false,"creators":["Martin, Patricia"],"institution":"Virginia Polytechnic Institute and State University","degree_name":"Ph. 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It was determined that the most efficient route to these ethers was not the most generally accepted route to ethers - the Williamson Reaction - but rather a solvolysis reaction between 1-bromo-1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene and the appropriate alcohol. Thermal rearrangement of the ethers had been expected to rearrange by a [1,5]-sigmatropic shift of the phenyl group in the 1-position to yield the corresponding enol ether. However, this appeared to occur only as a trace in some cases. Rather, the major product of the thermal rearrangements of these ethers was actually the elimination product, the hydrocarbon, 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene. The elimination is most likely the result of a retro-ene reaction."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Ph. D."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Investigation of the synthesis and thermal rearrangements of 1,2,3,4,5-Pentaphenyl-2,4,-Cyclopentadiene Alkyl Ethers"]}]}],"canonical_facts":{"dc:contributor.committeechair":["Ogliaruso, Michael A."],"dc:contributor.committeemember":["Bell, Harold M.","Mason, John G.","Hudlicky, Milos","Wightman, James P."],"dc:contributor.department":["Chemistry"],"dc:creator":["Martin, Patricia"],"dc:date.accessioned":["2014-08-13T14:38:37Z"],"dc:date.available":["2014-08-13T14:38:37Z"],"dc:date.issued":["1987"],"dc:description.abstract":["A comparative synthetic study of a series of six 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene alkyl ethers was investigated. 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