New Ring Expansion and Ring Opening Reactions of Vinyl Oxetanes and Vinyl Oxiranes

Persistent Link:
http://hdl.handle.net/10150/315543
Title:
New Ring Expansion and Ring Opening Reactions of Vinyl Oxetanes and Vinyl Oxiranes
Author:
Guo, Boying
Issue Date:
2014
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.
Embargo:
Release 11-Mar-2016
Abstract:
Three new synthetic methods employing vinyl oxetanes as substrates are presented. In Chapter 2, a new catalytic vinyl oxetane ring expansion is described. Origins, design, reaction, and optimizations are discussed. A novel asymmetric synthesis of 3,6-dihydro-2H-pyrans using chiral counterion catalysis is presented as part of these studies. In Chapter 3, the Z-selective ring opening of vinyl oxetanes using dialkyl dithiophosphate nucleophiles is described from initial discovery, through optimizations to the application towards the synthesis of thiopyrans. These insights were then utilized to develop a similar Z-selective protocol for vinyl oxiranes. In Chapter 4, a novel method to synthesize homoallylic alcohols from 3,6-dihydro-2H-pyrans using a mild and selective C-O reduction approach is described.
Type:
text; Electronic Dissertation
Keywords:
Chemistry
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Njardarson, Jon T.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen
dc.titleNew Ring Expansion and Ring Opening Reactions of Vinyl Oxetanes and Vinyl Oxiranesen_US
dc.creatorGuo, Boyingen_US
dc.contributor.authorGuo, Boyingen_US
dc.date.issued2014-
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.releaseRelease 11-Mar-2016en_US
dc.description.abstractThree new synthetic methods employing vinyl oxetanes as substrates are presented. In Chapter 2, a new catalytic vinyl oxetane ring expansion is described. Origins, design, reaction, and optimizations are discussed. A novel asymmetric synthesis of 3,6-dihydro-2H-pyrans using chiral counterion catalysis is presented as part of these studies. In Chapter 3, the Z-selective ring opening of vinyl oxetanes using dialkyl dithiophosphate nucleophiles is described from initial discovery, through optimizations to the application towards the synthesis of thiopyrans. These insights were then utilized to develop a similar Z-selective protocol for vinyl oxiranes. In Chapter 4, a novel method to synthesize homoallylic alcohols from 3,6-dihydro-2H-pyrans using a mild and selective C-O reduction approach is described.en_US
dc.typetexten
dc.typeElectronic Dissertationen
dc.subjectChemistryen_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.advisorNjardarson, Jon T.en_US
dc.contributor.committeememberNjardarson, Jon T.en_US
dc.contributor.committeememberGlass, Richarden_US
dc.contributor.committeememberMash, Eugeneen_US
dc.contributor.committeememberTomat, Elisaen_US
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