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Permanent link (DOI): https://doi.org/10.7939/R3CF9JJ5C

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Synthesis Towards Nitrogenous Model Bitumen Archipelagos Open Access

Descriptions

Other title
Subject/Keyword
quinolines
model asphaltenes
bitumen
reductive cross-electrophile coupling
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Reaugh, Devin J
Supervisor and department
Stryker, Jeffrey M (Chemistry)
Examining committee member and department
Brown, Alexander (Chemistry)
West, Frederick G (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2015-09-30T10:34:22Z
Graduation date
2015-11
Degree
Master of Science
Degree level
Master's
Abstract
The synthesis of functionalized quinolines is described herein. Utilizing condensation reactions, derivatized quinolines were prepared to serve as nitrogen-containing asphaltene islands. Basic halogenated phenylquinolines were synthesized via urea condensations. Highly substituted quinolines were prepared using a Brønsted acid-catalyzed Friedländer condensation. Benzophenone was used in combination with a variety of α-methylene ketones. A novel adaptation for acetophenone was developed. Individual islands were connected to alkyl tethers by reductive cross-electrophile coupling. Bromoarenes were coupled to α-bromo-ω-chlorooalkanes to install tethers with terminal chlorides. A cobalt-manganese catalyst-reductant system was first explored, and a second nickel-zinc system was refined for tether installation. Introductory experiments towards the use of these ω-chloro tethered islands in the synthesis of bis-functionalized ketones was briefly explored using Collman’s Reagent.
Language
English
DOI
doi:10.7939/R3CF9JJ5C
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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