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PHOTOLYSIS OF1-METHYL-9,10-ANTHRAQUINONE DERIVATIVES AND THEIR POTENTIAL REACTIVITY IN THE PHOTOENOL DIELS-ALDER REACTION

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title
PHOTOLYSIS OF1-METHYL-9,10-ANTHRAQUINONE DERIVATIVES AND THEIR POTENTIAL REACTIVITY IN THE PHOTOENOL DIELS-ALDER REACTION
author
Hilton, Gina M.
abstract
Functionalized 9,10-anthraquinones (AQ) have proven to undergo a Photoenol Diels-Alder (PEDA) reaction. The PEDA reaction has been enhanced by the following factors: increased AQ electron density and the geometry of the intermediate 1,4-biradical (BR). Hydrogen bonding of the intermediate BR aids the intermolecular Diels-Alder reaction upon the formation of the photo induced diene by preventing conversion back to starting material. A series of hydroxy, methyl, and methoxy substituted AQs were synthesized and photolyzed under 366 nm light. 1-Methyl-9,10-anthraquinone was photolyzed as a negative control due to a lack of electron density and inability to form an intramolecular hydrogen bond. Both 1,8-dimethyl-4-methoxy-9,10-anthraquinone, and 1,4-dimethoxy-8-methyl-9,10-anthraquinone produced the PEDA product when irradiated with dimethyl acetylenedicarboxylate in benzene. The hydroxy analogs of these compounds did not undergo the PEDA reaction and only produced starting material after irradiation. Characterization of the compounds was achieved by NMR, high-resolution Mass Spectrometry, and X-ray crystallography.
subject
Anthraquinones
Photochemistry
Photoenol Diels-Alder Reaction
contributor
Jones, Paul B (committee chair)
Colyer, Christa (committee member)
date
2014-01-15T09:35:19Z (accessioned)
2016-01-15T09:30:09Z (available)
2013 (issued)
degree
Chemistry (discipline)
embargo
2016-01-15 (terms)
identifier
http://hdl.handle.net/10339/39110 (uri)
language
en (iso)
publisher
Wake Forest University
type
Thesis

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