The investigation of an efficient synthesis of bicyclobutane and cyclobutane monomers

Persistent Link:
http://hdl.handle.net/10150/288996
Title:
The investigation of an efficient synthesis of bicyclobutane and cyclobutane monomers
Author:
Johnston, Keith Fox
Issue Date:
1999
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)
Keywords:
Chemistry, Organic.; Chemistry, Polymer.
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.titleThe investigation of an efficient synthesis of bicyclobutane and cyclobutane monomersen_US
dc.creatorJohnston, Keith Foxen_US
dc.contributor.authorJohnston, Keith Foxen_US
dc.date.issued1999en_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.abstractThe 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.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
dc.subjectChemistry, Polymer.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.proquest9934857en_US
dc.identifier.bibrecord.b3965235xen_US
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