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Permanent link (DOI): https://doi.org/10.7939/R3DR2PK95

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Application of Metallocarbene Decomposed from Diazoesters with Organic Azides and 1,2,3-Triazoles Open Access

Descriptions

Other title
Subject/Keyword
diazocarbonyl
metallocarbene
rhodium catalyst
triazole
azide
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Niu, Tianmin
Supervisor and department
West, Frederick G. (Chemistry)
Examining committee member and department
Hall, Dennis (Chemistry)
Clive, Derrick L. J. (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2016-02-08T09:27:36Z
Graduation date
2016-06
Degree
Master of Science
Degree level
Master's
Abstract
Metallocarbenes, in situ generated from catalytic decomposition of diazocarbonyl compounds, contain only 6 electrons at carbon center, therefore are highly electrophilic. Over the years, the metallocarbene intermediates have been continuously explored as a versatile tool toward C-C and C-X bond formations. An overview regarding the reactivities and typical transformations of metallocarbene species is discussed in Chapter 1. Chapter 2 discusses the use of organic azide as a nucleophile to intercept high-energy metallocarbene species. The α-imino ester was then generated in high yield. This transformation demonstrated a unique advantage over the traditional methods for α-imino ester synthesis since the only by-products are two equivalents of nitrogen gas. The subsequent trapping of α-imino esters with variety of carbon nucleophiles was also attempted to aim for generating α–quaternary amino esters; however, the process was not successful at the current stage. 1,2,3-Triazole compounds are one of the most important heterocycles in organic chemistry. From the past studies, these compounds are rather stable under oxidative, reductive, acidic and basic conditions due to its aromaticity. Chapter 3 illustrates a novel reactivity of stable 1,2,3-triazole compounds toward metallocarbenes, which process constructs a highly functionalized pyrroline-3-one heterocycles. A plausible reaction mechanism of this transformation has been rationalized yet inconclusive at current stage. The optimization and substrate scope of this reaction are detailed in Chapter 3.
Language
English
DOI
doi:10.7939/R3DR2PK95
Rights
This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for the purpose of private, scholarly or scientific research. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
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