The vast majority of theses in this collection are open access and freely available. There are a small number of theses that have access restricted to the WWU campus. For off-campus access to a thesis labeled "Campus Only Access," please log in here with your WWU universal ID, or talk to your librarian about requesting the restricted thesis through interlibrary loan.

Date of Award

Spring 2023

Document Type

Masters Thesis

Department or Program Affiliation

Chemistry Department of WWU

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Vyvyan, James R.

Third Advisor

Larsen, Michael B.

Abstract

With the recent discovery of an iodine mediated rearrangement of diallylsilanes, we set out to investigate a similar fluorine mediated rearrangement, aimed at introducing a new method for synthesizing organofluorine compounds. Interest in incorporating fluorine into organic molecules has grown significantly in recent years, primarily for medicinal applications. Since certain fluorination methods require the use of mCPBA, a common epoxidizing reagent, control experiments were performed on the reaction of several diallylsilanes with mCPBA, anticipating that a competing epoxidation of the diallylsilanes might occur. It was found that the formation of the hydroxy ester occurred through a regioselective epoxide opening from the carboxylic acid derivative of mCPBA. This was later mitigated by the addition of a basic buffer to yield the epoxysilanes. Various Lewis and Bronsted acids were screened to promote an intramolecular epoxide opening, however it was observed that Triethylamine trihydrofluoride (HF TEA) had complete regioselective fluoride ring opening of the given epoxide under mild conditions. To our knowledge this type of fluorine ring opening has not been described. Attachment of different ligands on silicon permits the tunability and activation of the so-called beta silyl effect. A range of epoxysilanes containing different groups on silicon were studied to investigate the rate, stereoselectivity, and further functionalization.

Type

Text

Keywords

Organic Chemistry, Fluorine, Silicon, Fluorohydrin, Fluorosilicon gauche effect

Publisher

Western Washington University

OCLC Number

1381270045

Subject – LCSH

Fluorination; Fluorine; Nucleophilic reactions; Chemistry, Organic

Format

application/pdf

Genre/Form

masters theses

Language

English

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

Rights Statement

http://rightsstatements.org/vocab/NKC/1.0/

Download

Included in

Chemistry Commons

Share

COinS