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    The investigation of an efficient synthesis of bicyclobutane and cyclobutane monomers

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    Author
    Johnston, Keith Fox
    Issue Date
    1999
    Keywords
    Chemistry, Organic.
    Chemistry, Polymer.
    Advisor
    Hall, H. K., Jr.
    
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    Publisher
    The University of Arizona.
    Rights
    Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
    Abstract
    The synthesis of bicyclobutane and cyclobutene monomers has been studied for the past 30 years. The polymers of these monomers have shown to possess superior properties in comparison to their linear analogs. Current synthetic methods used for the preparation of bicyclobutane and cyclobutene monomers require high temperature, high pressure, a large number of steps, and handling of toxic materials. Generally the synthetic methods employed have given very low yields. Dipolar [2+2]-cycloaddition reactions between alkenes take place spontaneously when one alkene contains strong donor substituents and the other strong acceptor substituents. Our general synthetic scheme involved a [2+2]-cycloaddition to form cyclobutane derivatives containing an acidic proton at C₃ or C₂ and an electron donating substituent at C₁. Following transformation of the donor substituent to a leaving group, bicyclobutanes or cyclobutenes were formed by 1,3- or 1,2-elimination. Phosphite, acetal, and amide as electron-donor substituents in [2+2]-cycloaddition reactions with cyano- or ester-substituted electrophilic alkenes form a variety of cycloadducts.
    Type
    text
    Dissertation-Reproduction (electronic)
    Degree Name
    Ph.D.
    Degree Level
    doctoral
    Degree Program
    Graduate College
    Chemistry
    Degree Grantor
    University of Arizona
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