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    THREE STUDIES OF 2-PYRIDONE PHOTOADDUCT REACTIVITY

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    Genre
    Thesis/Dissertation
    Date
    2010
    Author
    Chen, Peiling
    Advisor
    Sieburth, Scott McNeill
    Committee member
    Davis, Franklin A.
    Krow, Grant
    Department
    Chemistry
    Subject
    Chemistry, Organic
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/950
    
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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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