Syntheses and the Structures of Polymethylpolycyclic and Polycyclic "Cage" Molecules

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The structures of Diels-Alder cycloaddition of cyclopentadiene to 2,6-dimethyl-p-benzoquinone and methylcyclopentadiene to 2,6-dimethyl-p-benzoquinone were assigned by analysis of 1-D and 2-D proton and carbon-13 NMR spectra. The structures of the cycloadduct of methylcyclopentadiene to 2,6-dimethyl-p-benzoquinone and that of the corresponding intramolecular [2+2] photocyclization product were also obtained by single crystal X-ray structural analysis. As the second part of the study, a new polycyclic "cage" molecule, a substituted trishomocubane isomer, was synthesized. In this synthesis, reductive bond cleavage followed by Dieckmann condensation was employed. Wolff-Kishner reduction then was used to convert a β-keto ester "cage" molecule to the corresponding carboxylic acid. ... continued below

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v, 64 leaves : ill.

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Zhao, Dalian May 1989.

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This thesis is part of the collection entitled: UNT Theses and Dissertations and was provided by UNT Libraries to Digital Library, a digital repository hosted by the UNT Libraries. It has been viewed 13 times . More information about this thesis can be viewed below.

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  • Zhao, Dalian

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The structures of Diels-Alder cycloaddition of cyclopentadiene to 2,6-dimethyl-p-benzoquinone and methylcyclopentadiene to 2,6-dimethyl-p-benzoquinone were assigned by analysis of 1-D and 2-D proton and carbon-13 NMR spectra. The structures of the cycloadduct of methylcyclopentadiene to 2,6-dimethyl-p-benzoquinone and that of the corresponding intramolecular [2+2] photocyclization product were also obtained by single crystal X-ray structural analysis. As the second part of the study, a new polycyclic "cage" molecule, a substituted trishomocubane isomer, was synthesized. In this synthesis, reductive bond cleavage followed by Dieckmann condensation was employed. Wolff-Kishner reduction then was used to convert a β-keto ester "cage" molecule to the corresponding carboxylic acid. A compound that possesses twofold symmetry was isolated from reaction product mixture. The structure of this compound has been established by single crystal X-ray crystallography.

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v, 64 leaves : ill.

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UNT Theses and Dissertations

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  • May 1989

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  • March 9, 2015, 8:15 a.m.

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  • Nov. 14, 2017, 10:37 a.m.

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Zhao, Dalian. Syntheses and the Structures of Polymethylpolycyclic and Polycyclic "Cage" Molecules, thesis, May 1989; Denton, Texas. (digital.library.unt.edu/ark:/67531/metadc500344/: accessed December 17, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; .