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.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc500344 |
| Date | 05 1900 |
| Creators | Zhao, Dalian |
| Contributors | Marchand, Alan P., Schwartz, Martin |
| Publisher | University of North Texas |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | v, 64 leaves : ill., Text |
| Rights | Public, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved., Zhao, Dalian |
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