Synthesis Towards Nitrogenous Model Bitumen Archipelagos

• Author / Creator

  Reaugh, Devin J

• 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.

• Subjects / Keywords

  • Model asphaltenes
  • Reductive cross-electrophile coupling
  • Bitumen
  • Quinolines

• Graduation date

  Fall 2015

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/R3CF9JJ5C

• License

  This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. 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.