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    • Graduate School - MU Theses and Dissertations (MU)
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    • 2015 Dissertations (MU)
    • 2015 MU dissertations - Access restricted to UM
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    The [2,3]-sigmatropic rearrangement of propargylic sulfonates to allenic sulfones and further applications to oxacycles and dihydrofuranones

    Tata, Rama Rao
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    Date
    2015
    Format
    Thesis
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    Abstract
    [ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT REQUEST OF AUTHOR.] The scope of [2,3]-sigmatropic rearrangement of propargylic sulfinates to allenic sulfones by silver catalysis was expanded. A series of new propargylic sulfinate esters was generated from a variety of aromatic and heteroaromatic sulfonyl chlorides and their rearrangement to allenic sulfones is reported. In addition, the synthesis of propargylic sulfinate esters containing electron-withdrawing benzenesulfonyl chlorides was optimized and reported. In the course of pursuing a Nazarov cyclization of allenyl vinyl ketones (AVK), we discovered multiple new reactions. Allenyl alcohols underwent an intramolecular cyclization to 2,5-dihydrofurans in the presence of Fetizon's reagent and this process was then optimized using silver fluoride. The methodology was expanded to synthesize higher membered oxacycles also. A tandem cyclization of hydroxypropargylic sulfinate esters to 2,5-hydrofurans was also developed. A new synthesis of a'-hydroxyenones was developed by the oxidation of a-allenyl alcohols with Cr (VI) regents and then extended to synthesize dihydrofuran- 3(2H)-ones by acid catalysis.
    URI
    https://hdl.handle.net/10355/50142
    https://doi.org/10.32469/10355/50142
    Degree
    Ph. D.
    Thesis Department
    Chemistry (MU)
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    Access is limited to the campuses of the University of Missouri.
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    • 2015 MU dissertations - Access restricted to UM
    • Chemistry electronic theses and dissertations (MU)

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