• Login
    View Item 
    •   Shocker Open Access Repository Home
    • Graduate Student Research
    • ETD: Electronic Theses and Dissertations
    • Master's Theses
    • View Item
    •   Shocker Open Access Repository Home
    • Graduate Student Research
    • ETD: Electronic Theses and Dissertations
    • Master's Theses
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Proof of concept for the synthesis of [3.4.3.4] metacyclophane using a porphyrin as a scaffold

    View/Open
    Thesis (3.003Mb)
    Date
    2008-05
    Author
    Jayne, Charles L.
    Advisor
    Burns, Dennis H.
    Metadata
    Show full item record
    Abstract
    Several endo- and exo- cyclophanes of various annulus sizes have been synthesized in the past without the benefit of a template and yields were considered moderate to good. The yields of the exo- cyclophanes were better than the endo- due to “self templating”. Wishing to improve yields of the endo- cyclophanes, we have incorporated into its synthetic scheme a porphyrin as a template to direct the macrocycle’s formation. Incorporating a [2+2] synthetic scheme, half of the cyclophane is synthesized by reacting two equivalents of 2-bromoanisole and one equivalent of 1,3-alkyldiol bistosylate through a high yield Grignard reaction coupled by our copper catalyst. The para positions of the bis-anisole are then functionalized to protect the para position from a Claisen rearrangement later in the scheme and also to allow flexibility for elaboration once finished. The bis-phenol is deprotected from the bis-anisole. The newly exposed phenols are allylated and rearranged to give the bis-ortho elaborated bis-phenol. Using a tetra-alpha-5,10,15,20-tetrakis(2-aminophenyl)porphyrin as the basic scaffold, its amino groups were transformed into isocyanates. In situ, the isocyanates were reacted with our ortho-elaborated bis-phenol to rigidly secure two sides of the cyclophane to the porphyrin by way of the newly formed carbamate groups. The bisortho-olefins are then metathesised using Grubbs’ second generation catalyst furnishing the cyclophane ring.
    Description
    Thesis [M.S.] - Wichita State University, College of Liberal Arts and Science, Dept. of Chemistry
    URI
    http://hdl.handle.net/10057/2052
    Collections
    • CHEM Theses and Dissertations
    • LAS Theses and Dissertations
    • Master's Theses

    Browse

    All of Shocker Open Access RepositoryCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsBy TypeThis CollectionBy Issue DateAuthorsTitlesSubjectsBy Type

    My Account

    LoginRegister

    Statistics

    Most Popular ItemsStatistics by CountryMost Popular Authors

    DSpace software copyright © 2002-2023  DuraSpace
    DSpace Express is a service operated by 
    Atmire NV