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THREE STUDIES OF 2-PYRIDONE PHOTOADDUCT REACTIVITY

Chen, Peiling
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Thesis/Dissertation
Date
2010
Advisor
Sieburth, Scott McNeill
Committee member
Davis, Franklin A.
Krow, Grant
Group
Department
Chemistry
Subject
Chemistry, Organic
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http://hdl.handle.net/20.500.12613/950
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Chen_temple_0225E_10253.pdf
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DOI
http://dx.doi.org/10.34944/dspace/932
Abstract
2-Pyridones such as iii undergo efficient [4+4] photocycloaddition reactions, yielding strained tricyclic cyclooctadiene structures iv and v, with functionality at every carbon. As part of a program to develop the chemistry of these complex adducts, three studies have been conducted. Halogenation of trans iv give rearranged i. Cope rearrangement of cis v gives vi which can undergo retro-Mannich reaction to yield unsymmtrically coupled piperidines vii. Pyridones can also undergo photo-[4+4] reactions with furans. Cycloaddition of viii yields ix. Transannular closure of ix produces triquinane x, a model system for total synthesis of crinipellin A xi.
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