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Permanent link (DOI): https://doi.org/10.7939/R3QR4P20N

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Generation and Trapping of Highly Strained Reactive Intermediate: Ethyl 1,2-Cyclohexadienecarboxylate Open Access

Descriptions

Other title
Subject/Keyword
1,2-cyclohexadiene
cyclic allene
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Zhou, Sida
Supervisor and department
Frederick, West (chemistry)
Examining committee member and department
Derrick, Clive (chemistry)
Rylan Lundgren (chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2015-07-06T09:32:18Z
Graduation date
2015-11
Degree
Master of Science
Degree level
Master's
Abstract
Highly strained reactive intermediates can initiate chemical reactions and afford unique products. Cyclic allenes are important examples of such intermediates. Within the cyclic allene family, 1,2-cyclohexadiene was intensively studied over the years. In this dissertation, the investigation of developing practical methodology to generate and trap 1-substituted-1,2-cyclohexadiene will be detailed. In Chapter 1, a brief history of strained reactive intermediates family is discussed, including benzynes and cycloalkynes, in addition to the development of 1,2-cyclohexadiene chemistry. The discovery of 1,2-cyclohexadiene, the study on its structure and properties and some known 1-substituted cyclohexa-1,2-dienes will be discussed. A brief introduction of existing methods to generate and trap 1-subsituted cyclohexa-1,2-diene is described at the beginning of Chapter 2. Investigation of practical generation and trapping of ethyl 1,2-cyclohexadienecarboxylate, including systematic optimization of reaction conditions and exploration of the reaction scopes, is then discussed. The attempt to investigate the mechanism of newly discovered [2+2] cycloaddition between ethyl 1,2-cyclohexadienecarboxylate and alkynes will also be included.
Language
English
DOI
doi:10.7939/R3QR4P20N
Rights
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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