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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 …