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Aryne Reactions in the Synthesis of Heterocyclic Molecules


Haley, Christopher Keating (2016) Aryne Reactions in the Synthesis of Heterocyclic Molecules. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z9QN64P5.


Reactive intermediates play an important the within the realm of chemical synthesis. Their high energy and transient nature make them difficult to observe and characterize, but it is these same properties that empower them to form bonds traditionally seen as difficult to prepare and unusual architectures quickly and efficiently. Herein, two reactive intermediates, arynes and transitient (2azaaryl)-cuprates, are exploited for their abilities to prepare important chemical motifs. Both serve as an avenue into the functionalization of arenes to provide products which hold value in a variety of fields including natural product total syntethis, pharmaseuticals and ligand design.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Aryne, Total Synthesis, Chemistry, Organic Chemistry, Benzyne, heterocycle
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Dougherty, Dennis A. (chair)
  • Agapie, Theodor
  • Reisman, Sarah E.
  • Stoltz, Brian M.
Defense Date:2 December 2015
Record Number:CaltechTHESIS:05252016-185612554
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:9760
Deposited By: Christopher Haley
Deposited On:26 May 2016 19:22
Last Modified:08 Nov 2023 00:39

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