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Cyclopentadienone Conversions To Terephthalates And Cycloadditions Of Alkynes And Azides, Sarah E. Bragg
Cyclopentadienone Conversions To Terephthalates And Cycloadditions Of Alkynes And Azides, Sarah E. Bragg
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Cyclopentadienone derivatives can be converted via a Diels-Alder reaction to multifunctional terephthalate derivatives, which can then be converted to poly(phenylene vinylene) derivatives. It was demonstrated that terephthalate derivatives can be simply and reproducibly synthesized from 2,5-diethoxycarbonyl-3,4-diphenylcyclopentadienone with a variety of acetylenes, having yields ranging from 63% to quantitative yields. The terephthalate derivatives synthesized varied from oils to crystalline solids, but were readily isolated and generally had high rates of completion despite expected steric factors. Terephthalate derivatives with pendent acetylenes were formed in reactions with as low as a 3:1 ratio of diacetylene to cyclopentadienone. A terephthalate derivative with a pendent …
Synthesis Of Fluorinated Indenofluorenediones And Bis(2-Fluorophenyl) Substituted Ppv, Jeffrey D. Fogle
Synthesis Of Fluorinated Indenofluorenediones And Bis(2-Fluorophenyl) Substituted Ppv, Jeffrey D. Fogle
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The compound 2,5-di(ethoxycarbonyl)-3,4-di(2-fluorophenyl)cyclopentadienone was successfully synthesized and led to the synthesis of terephthalates, di(hydroxymethyl)s, di(chloromethyl)s, diacids, diacid chlorides and indenofluorenediones having the pendent groups null, hexyl and 2-(4-benzothiazolyl)phenyl. All new compounds were characterized by melting point, IR, 1H NMR, 13C NMR, 19F NMR, GC/MS and combustion analysis. Most of the forementioned compounds showed an indication of restricted rotation with the appearance of trans and cis diastereomers. The asymmetric compounds showed the occurrence of four isomers. In some spectra, signals corresponding to all four isomers were visible. Through-space 1H-19F, 13C-19F and 19F-19F coupling was observed for most compounds in 1H NMR, …