Open Access. Powered by Scholars. Published by Universities.®
Physical Sciences and Mathematics Commons™
Open Access. Powered by Scholars. Published by Universities.®
Articles 1 - 2 of 2
Full-Text Articles in Physical Sciences and Mathematics
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
Browse all Theses and Dissertations
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 …
The Synthesis, Reduction, And Chlorination Of 5-Alkoxy-2,3-Diphenylterephthalates, Rachel Marie Sayers
The Synthesis, Reduction, And Chlorination Of 5-Alkoxy-2,3-Diphenylterephthalates, Rachel Marie Sayers
Browse all Theses and Dissertations
A series of alkoxy, phenylated terephthalates has been synthesized as monomer precursors to the corresponding poly(phenylene vinylene)s (PPV). The hydroxy, phenylated terephthalate was synthesized via: 1) a Diels-Alder cycloaddition between an ethynyl boronic ester and a cyclopentadienone (CPD) with subsequent hydrolysis/oxidation of the boronate ester or 2) a Diels-Alder cycloaddition between vinylene carbonate and CPD followed by thermolysis of the bridged adduct. The hydroxy, phenylated terephthalate was alkylated via a phase-transfer reaction with iodomethane, propargyl bromide, benzyl chloride, allyl bromide, and bromobutane to produce the alkoxy, phenylated terephthalates in yields from 38.6- 91.1%. The alkoxyterephthlates were reduced with lithium aluminum …