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Date Permissions Signed
8-6-2018
Date of Award
Summer 2018
Document Type
Masters Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
O'Neil, Gregory (Gregory W.)
Second Advisor
Vyvyan, James R.
Third Advisor
Antos, John M.
Abstract
Herein, we report new allylation reactions using ring-strained allylalkoxysiletanes. These reactions can achieve high yield and have high chemoselectivity, as evidenced by carefully designed substrates. Based on previous evidence, we propose that the reaction proceeds through an exchange mechanism, where first the alkoxy group of the siletane exchanges with the hydroxyl group of the substrate, followed by coordination of the substrate carbonyl to the siletane, and then intramolecular allylation of the carbonyl.
Type
Text
Keywords
silanes, carbonyl, allylation, chemoselective
DOI
https://doi.org/10.25710/kzb4-1r14
Publisher
Western Washington University
OCLC Number
1048259448
Subject – LCSH
Silane compounds; Carbonyl compounds; Nucleophilic reactions; Grignard reagents; Organic compounds--Synthesis; Catalysts
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 thesis for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.
Recommended Citation
Cummins, Elizabeth J. (Elizabeth Jane), "New Reactions of Ring Strained Allyl Silanes" (2018). WWU Graduate School Collection. 749.
https://cedar.wwu.edu/wwuet/749