TETRAMETHYLENE INTERMEDIATES IN POLYMERIZATION AND CYCLOADDITION REACTIONS

Persistent Link:
http://hdl.handle.net/10150/281942
Title:
TETRAMETHYLENE INTERMEDIATES IN POLYMERIZATION AND CYCLOADDITION REACTIONS
Author:
Rasoul, Husam Ali Abdul
Issue Date:
1981
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:
Five tri- and tetra-substituted electron-poor olefins containing a β-leaving group, initiated cationic polymerization of p-methoxystyrene with widely varying results. As the electrophilicity of the electron-poor olefins increased, the yields and molecular weights of the polymers formed decreased. The same was true when the excellent leaving group, trifluoromethanesulfonate, was replaced by the poorer leaving group, chloride. Another series of tri-substituted olefins was prepared and reacted with p-methoxystyrene in the presence of excess methyl methacrylate or styrene. Terpolymer was formed as a major product when the electron-poor olefin used contained an α-ester group. The yield of the terpolymer increased with the increasing electrophilicity of the electron-poor olefin. The reactions of methyl α-cyanoacrylate with a number of electron-rich olefins were also studied and found to give new types of adducts, such as Diels-Alder adducts and pyrans. All these reactions were suggested to go through the formation of a tetramethylene intermediate, a resonance hybrid of a zwitterion and spin paired biradical.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Alkenes.; Carbenes (Methylene compounds); Polymerization.; Polymers.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Hall, H. K. Jr.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleTETRAMETHYLENE INTERMEDIATES IN POLYMERIZATION AND CYCLOADDITION REACTIONSen_US
dc.creatorRasoul, Husam Ali Abdulen_US
dc.contributor.authorRasoul, Husam Ali Abdulen_US
dc.date.issued1981en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © 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.en_US
dc.description.abstractFive tri- and tetra-substituted electron-poor olefins containing a β-leaving group, initiated cationic polymerization of p-methoxystyrene with widely varying results. As the electrophilicity of the electron-poor olefins increased, the yields and molecular weights of the polymers formed decreased. The same was true when the excellent leaving group, trifluoromethanesulfonate, was replaced by the poorer leaving group, chloride. Another series of tri-substituted olefins was prepared and reacted with p-methoxystyrene in the presence of excess methyl methacrylate or styrene. Terpolymer was formed as a major product when the electron-poor olefin used contained an α-ester group. The yield of the terpolymer increased with the increasing electrophilicity of the electron-poor olefin. The reactions of methyl α-cyanoacrylate with a number of electron-rich olefins were also studied and found to give new types of adducts, such as Diels-Alder adducts and pyrans. All these reactions were suggested to go through the formation of a tetramethylene intermediate, a resonance hybrid of a zwitterion and spin paired biradical.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectAlkenes.en_US
dc.subjectCarbenes (Methylene compounds)en_US
dc.subjectPolymerization.en_US
dc.subjectPolymers.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorHall, H. K. Jr.en_US
dc.identifier.proquest8116687en_US
dc.identifier.oclc7797558en_US
dc.identifier.bibrecord.b1353709xen_US
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