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    THERMAL RING OPENING OF CYCLOPROPANES AS INITIATORS FOR POLYMERIZATION

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    Author
    Willis, Terrance James, 1959-
    Issue Date
    1987
    Keywords
    Cyclopropane.
    Alkenes.
    Polymers.
    
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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
    Donor-Acceptor tetramethylenes have been studied by polymerizations. 1,4-Zwitterionic intermediates are indicated when reactive tetramethylenes initiate homopolymerization. Alternately, 1,4-diradical intermediates initiate copolymerization. This basis for studying intermediates has led to an empirical table for predicting the zwitterionic and diradical nature of addition and polymerization reactions of tetramethylenes. Here we attempted to extend this work to trimethalylenes by studying the thermal ring opening of ethyl chrysanthemate, ethyl 1-cyano-2-(4-methoxyphenyl)-cyclopropane-corboxylate, ethyl 1-cyano-2-(2-methoxyphenyl)-cyclopro-panecroboxylate, and diethyl 1,3-dicyano-w,r-di(2-methoxyphenyl)-cyclobutanedicarboxylate. These compounds were found to be thermally stable to 150°C and did not initiate polymerization in styrene, methyl methacrylate, a series of high boiling acrylates, and dimethyl fumarate. Free radicals were trapped in dimethyl fumarate to give oligomers at temperatures above 110°C. Even though the compounds studied did not initiate polymerization at decomposition temperatures of 175°-200°C, dimethyl fumarate may prove useful in these studies in the future.
    Type
    text
    Thesis-Reproduction (electronic)
    Degree Name
    M.S.
    Degree Level
    masters
    Degree Program
    Graduate College
    Chemistry
    Degree Grantor
    University of Arizona
    Collections
    Master's Theses

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