Publication Date
2019
Document Type
Dissertation/Thesis
First Advisor
Klumpp, Douglas A.
Degree Name
M.S. (Master of Science)
Legacy Department
Department of Chemistry and Biochemistry
Abstract
This thesis describes a coupling reaction involving cationic charge delocalization. This work began as a study of the Piancatelli rearrangement, a reaction involving furan-based triaryl methyl cations. A new synthetic reaction has been discovered using these furan-based triaryl methyl cations as electrophilic intermediates. Zinc chloride has been found to be an effective Lewis acid catalyst for the ionization of the triaryl methanols to the carbocations. It has been found that furan-based triaryl methyl cations react with nucleophiles such as enol silyl ethers and silyl ketene acetals. Similar to the Piancatelli reaction, nucleophilic reactions are found to occur at the 5-position of the furan ring. This is consistent with a mechanism involving carbocation charge delocalization through the furan ring. Despite the nucleophilic reaction, the rearrangement does not occur. Different triaryl methanol compounds and nucleophiles were examined.
Recommended Citation
Xue, Hongfang, "Coupling Reactions of Triaryl Carbocations Via Cationic Charge Delocalization" (2019). Graduate Research Theses & Dissertations. 7794.
https://huskiecommons.lib.niu.edu/allgraduate-thesesdissertations/7794
Extent
143 pages
Language
eng
Publisher
Northern Illinois University
Rights Statement
In Copyright
Rights Statement 2
NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.
Media Type
Text
