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Date of Award

Spring 2023

Document Type

Masters Thesis

Department or Program Affiliation

Chemistry Department of WWU

Degree Name

Master of Science (MS)



First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Vyvyan, James R.

Third Advisor

Larsen, Michael B.


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.




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


Western Washington University

OCLC Number


Subject – LCSH

Fluorination; Fluorine; Nucleophilic reactions; Chemistry, Organic




masters theses




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